


Fifty Fix-its

by Dancingdog



Category: Supernatural
Genre: 15x19, Canon Compliant, Coda, F/M, Fix-It, M/M, Plot Hole Fix, Prompt Challenge, lots of plot holes
Language: English
Status: In-Progress
Published: 2020-11-17
Updated: 2021-01-22
Packaged: 2021-03-10 05:02:48
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 8
Words: 25,763
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27608051
Author URL: https://archiveofourown.org/users/Dancingdog/pseuds/Dancingdog
Summary: Fifty unrelated endings for the final season of Supernatural.A.K.A a prompt word challenge set byLuckyFlucky934.Thanks, buddy, for giving me such deep and thought-provoking prompts.-----Ch 8 excerpt:He squinted and took in the exhaustion behind Dean’s eyes. “How many times have you been through this, Dean? How many times have you… died and been hurled back through time?”Dean laughed hollowly. “Too many. I don’t know. Lost count.”
Relationships: Castiel/Dean Winchester, Eileen Leahy/Sam Winchester
Comments: 68
Kudos: 70





	1. Clowns

_Clowns; the lot of them,_ thought Chuck with an amused smirk as he waited for the Impala to coast out of view. He picked himself up off the ground and dusted off his jacket. 

_Didn’t they understand what he was? Did they really think that Jack – a_ child _– would be able to contain all that raw power?_

Chuck laughed softly to himself and glanced around. He could hear birds beginning to sing to each other amidst the trees and he knew that the young Nephilim had already begun piecing the world back together, one creature at a time. Soon, he would undo all of Chuck’s work – including the destruction of the other universes. Jack would bring them all back because in his young, righteous mind, it was the right thing to do. 

He would break Sam and Dean’s hearts too – would leave them in the middle of an ordinary street with nothing but a smile and a promise that he would be a ‘hands-off’, all-powerful deity. 

He would repopulate Heaven with Angels who adored humanity and he would steal Castiel back from The Empty because the kid couldn’t stand the thought of leaving his ‘father’ in such a desolate place. 

He would listen to prayers and maybe offer a little divine intervention to those who really needed it.

He would be a good ruler. A kind and just ruler. He would be the sort of god that Sam and Dean and Castiel expected of him. 

…For about a year.

And then all of his power would disperse and return to its original owners. After all, Jack was only renting those powers – Billie’s spell was temporary and eventually, the magic from Adam’s rib would be used up and all that power would come crashing out of him like a broken dam, seeking its original hosts. Since Michael and Lucifer were dead and Chuck had created them both, that meant that all of Jack’s borrowed power would return to him. 

And Jack would burn from the inside out.

Chuck smiled as a bluebird fluttered to the ground beside him and began collecting twigs and leaf litter for its nest. It was a pretty little thing, with a red breast and vibrant blue wings. 

Jack would die in tremendous pain and Chuck would return to his rightful place. It was a wonderful thought; Castiel and the Winchesters would be so _devastated_. 

And then he’d finally be able to kill them all.

Did they honestly believe that they’d won? Chuck had created _everything_ , including humans and Angels. Including _Lucifer_. He’d created the act of human-Angel copulation and the resulting offspring. He knew every single property of a Nephilim and all of their limitations. 

Didn’t they understand that this was all part of his story?

He blinked and watched the bluebird disintegrate. 

He would get his perfect ending; he just had to wait another year. He was good at waiting.

He glanced up to the sky and waved, a cheeky grin settling on his face. 

Jack was watching him. He could feel it.

 _Clowns,_ he thought with a chuckle.

**Notes for the Chapter:**

> After being mildly disappointed and confused after 15x19, my friend and housemate set me a challenge to write 50 shorts to 50 words she came up with. Each must be unrelated and should be written as a potential ending to the show. They can tie up loose ends, fill in plot holes, or go in completely unexpected directions, but they must be endings. The challenging part is trying to fit them into canon and make them at least semi-believable. Hope you enjoy this mess, 'Flucky'.
> 
> Also, to anyone who wants to take on this challenge with me, the chapter titles are the prompts!


	2. Apron

“I can’t believe you’re still wearing that thing.” 

Dean glanced down at the white apron strung low around his hips. He looked up at Sam with a grin.

“Hey, burger grease _stains_ – Meat Man’s gotta wear his uniform.” 

Sam shook his head, nose wrinkled. “That still doesn’t mean what you think it means.”

“Shut up,” snorted Dean before placing a burger delicately onto a bun. He decorated it with lettuce and tomatoes and cheese with careful precision before setting the remaining half of the bun on top of his magnificent creation. Then he held the plate out to Sam. “Your tastebuds will thank me.” 

Sam rolled his eyes good naturedly and disappeared from the room with a bounce in his step that Dean equated to excitement. His brother might mock him, but Dean knew that Sam enjoyed his home-cooking. 

He returned to dressing his own burger in silence.

The bunker was quiet these days; two people didn’t take up very much room and when Sam was on his dates with Eileen, the bunker felt even larger, emptier. Dean missed hearing Jack shuffling around, raiding nougat and chocolate from the cupboards in the dead of night when he thought that no one could hear him. He missed the kid’s constant questions and the movies they watched together. 

He’d said that Jack wasn’t family, but he’d lied. He’d had to lie – to Sam and himself. The prospect of losing Jack had shattered him enough and he wasn’t allowed to break; not with billions of lives at stake. Chuck had been willing to kill the _entire world_ and Jack had been the only person able to stop him. He’d yelled that Jack wasn’t family because he’d needed to distance himself; prepare himself for the inevitable moment that they lost him. He’d believed that doing so would reduce the pain of Jack’s death, but as it turned out, he’d been wrong. 

Jack might not have died, but there was still a hole in his heart.

At least the kid was alive. 

Dean closed his eyes for a moment to ground himself. Not everyone in their family had been so lucky.

Technically, there were two holes in Dean’s heart – one that ached with longing and another that resembled a deep, bottomless pit of agony. Each night, he would think about that second hole and its cause, and he would feel himself drowning, sucking in lungfuls of air until his head swam and he could see nothing but darkness as the silence swallowed him whole. 

Dean cleared his throat to distract himself. He would pull himself together eventually, as he always did. Or he would bury the feelings so deep into his personal chest of repressed emotions that he wouldn’t have to deal with them for another decade. As he always did. As a certain Angel had apparently done with his own intense feelings. 

Sam was probably worried about his inability to talk about their missing family member but then again, Sam was always worried about something. Fortunately, he had Eileen to distract him and give him a life he deserved after all he had faced. And Dean, well… 

He had memories.

And that’s all he’d ever have, now. 

That crushing feeling in his chest had returned and he cast his gaze to the ceiling, ignoring the way his eyes prickled.

“Nice apron.”

His spatula clattered against the countertop and he whirled around with wide eyes, apron flapping around his knees. He’d know that voice anywhere. 

“Hello, Dean,” Castiel greeted from the doorway.

Something snapped in Dean’s chest and he stumbled forwards before dragging the Angel into a tight hug. 

“Never again,” he whispered beside Castiel’s ear as tentative arms slid around him. “Don’t ever do that again.”

Castiel was quiet for a long moment before timidly asking, “Which part?” 

“Dying,” Dean growled fiercely. “Sacrificing yourself _again_. Man, you have _got_ to stop doing that.”

Castiel fell limp and Dean held onto him a little longer. He pressed his face into the shoulder of the familiar trench coat and just _breathed_. He could feel the pit in his heart closing as quickly as it had been ripped open. 

After a few moments, Castiel shifted uncomfortably. “…About what I said-” 

“Stop,” Dean interrupted tiredly as he slid his arms inside Castiel’s coat and clung to him. “Just… stop.” He closed his eyes as a sense of calm washed over him. The bunker suddenly didn’t seem so empty anymore. “It’s great to have you home, Cas.” 

Castiel fell quiet and squeezed Dean gently. “…It’s great to be home.”

Dean smiled. He didn’t care how or why Cas was here, only that he was. 

“We should probably show Sam the good news,” Dean hummed as he leaned backwards to take a look at the Angel. He appeared unscathed and another part of Dean relaxed at that knowledge. 

“That would be sensible,” Castiel agreed, looking slightly red-faced.

“Awesome,” grinned Dean as he pointedly slotted his hand into Castiel’s and led him out of the kitchen. 

Castiel’s cheeks burned, eyes as wide as saucers, but when Dean deposited him in front of Sam and refused to release his hand, Dean caught the surprised joy dancing in his gaze. 

Sam dropped his burger on his lap, jaw slack as he stared up at Castiel.

Dean beamed and gestured to the mess of cheese and meat staining Sam’s jeans.

“And that, Sammy, is why I wear an apron.”


	3. Dog

“So much for you hating dogs,” Castiel snorted as the shaggy beast stretched out over Dean’s lap – and the rest of the couch. 

Dean stroked its head affectionately as it cracked an eye open to gaze disinterestedly at Castiel.

“He’s mostly Sam’s dog,” Dean protested. “He’s always wanted one, ever since he was a kid.” 

Castiel shot Dean an unimpressed stare. “Which is why he spends all of his waking life at your heel?”

The tan hound yawned before nestling back into Dean’s warmth. Castiel narrowed his eyes at the creature as something dangerously close to jealousy swirled around the pit of his stomach. He swore that dog had a personal mission to snatch Dean’s attention away from him. 

Dean must have caught the look in his eye, for his lips twitched into what might have been a smile had he not forced his expression immediately into neutrality. He sidled along the couch subtly. Castiel took the seat, attempting to look dignified and not at all like he was envious of a stray dog. 

He smiled as Dean slid an arm around him. Silence accompanied the movement.

“He’s got nowhere else to go,” Dean commented. “And he didn’t exactly put up a fuss when I put him in the car the first time.” 

_The first time_ ; before he had disintegrated at Chuck’s hands. Castiel’s gaze softened as he recalled the poorly-concealed pain in Dean’s eyes when he had recounted the story. He had been dead at that point and suddenly, so had everyone else, except for the hairy mutt on Dean’s lap. And then Chuck had taken him too, determined to extinguish every last shred of hope the Winchesters had clutched onto. 

Had it only been four months since then?

Castiel leaned into Dean’s side casually and neither of them said anything about the rather intimate position. 

The dog gazed at Castiel with dark eyes. It placed a paw on the Angel’s thigh and _shoved_.

“Why does he hate me?” Castiel asked in exasperation, determined not to relinquish his position at Dean’s side. “Animals don’t usually hate Angels.” 

Dean couldn’t quite hide the smile this time. “It’s probably the smell.”

He received a withering glare. “Rude.” 

A warm, joyful grin brightened Dean’s face and he squeezed Castiel’s hip ever-so-slightly until the Angel’s glare melted away. 

Dark eyes narrowed and suddenly, the hairy beast on Dean’s lap sprung upwards to lick at his face insistently. Dean laughed and was forced to slide his arm away from the frowning Angel in order to wrestle the dog into a more sensible position. 

“Scooby, stop. Down boy, come on, down,” Dean snorted as Castiel scowled at the creature.

Eventually, Scooby settled against Dean’s side. 

The side that Castiel had been pressed into mere moments ago.

Scooby glanced at Castiel through the corner of his eye with what Castiel thought was a rather haughty expression. He pressed his lips together and considered shoving the irritating creature off the couch. 

“Who’s a good boy?” Dean cooed, ruffling the dog’s head enthusiastically. Scooby played up to the attention; panting through a wide grin and whipping his tail heavily against Castiel. 

Castiel's lips drew into a thin line. If he was human, that tail would have hurt but as it was, he merely found the motion irksome. He grabbed Scooby’s tail in order to still it. 

Scooby yelped, flinching as he swivelled his head to whine pathetically at Castiel.

Predictably, Dean played right into the beast’s paws. 

“Cas, man, you’re hurting him,” Dean said with a disapproving frown.

Castiel glanced at the light grip he held on Scooby’s tail. “He’s being dramatic,” he huffed as he released the dog. Scooby snuggled deeper into Dean’s side with a quiet whimper. 

“What did he do to you?” Dean coddled as he toyed with Scooby’s ears. “What did he do to my best bud?”

Scooby perked up and stood, eyes twinkling with excitement as his tail beat Castiel’s face repeatedly. 

“Sam’s dog, huh?” Castiel asked, hoping he didn’t sound quite as bitter as he felt.

Dean rolled his eyes and pointedly ignored Castiel as he continued to fuss over Scooby. After a few moments, he stood and Scooby leapt to the floor and stared up at Dean obediently, waiting for instruction. 

Dean chuckled and scratched a floppy ear. “I’m just going to take a leak, bud. I’ll be back in a sec.”

Castiel watched him leave and once he was sure that Dean was out of hearing range, he turned to Scooby with an accusing glower. 

“I’m onto you,” he whispered before standing and heading into the kitchen for a strong coffee.

* * *

Scooby’s tail slowed to a stop once he was certain that the human was out of hearing range. He glanced at the Angel with what he hoped was a smug grin and was delighted to find the Angel glowering at him. 

He enjoyed riling the Angel.

“I’m onto you,” the Angel hissed at him before striding away in that irritatingly dramatic way of his; trench coat tails billowing behind him. 

Scooby hopped onto the couch once more and stretched over it with a self-satisfied growl. It wasn’t that he preferred the human over the Angel – not at all.

He hated them both equally.

The floppy-haired human was marginally better, but he still wasn’t Scooby’s favourite being. 

Unfortunately, The Master Of All Things had given him a job and although he was loath to admit it, he was terrified of The Master. The Master could seriously hurt him; destroy him, even. And he very much did not want to be destroyed. 

Out of all his brothers and sisters, he had been chosen for a very important mission. Under The Master’s orders, he was to protect the Winchesters and the Angel Castiel from all the monsters left on Earth, and he was to do so without revealing his true nature. 

The Master had dragged him from his home and asked for his aid. Sensing the power swirling within The Master, Scooby had wisely chosen to offer his services and The Master had smiled, as though he wasn’t capable of destroying the entire universe with a snap of his fingers. 

It turned out that The Master did not wish to eliminate all monsters on Earth as he understood that there were as many good monsters as there were evil. However, he had been troubled, for he was aware that one of his favourite humans would meet a horrific fate, even with the presence of the annoying Angel. 

It was Scooby’s job to prevent that from happening. No monster, Demon, or Angel was to harm the Winchesters and their Angel whilst Scooby was by their side. 

So, like a good dog, Scooby obeyed orders and protected his charges from all that threatened them, even if they weren’t entirely aware of it; under no circumstances was he allowed to reveal his true form. 

After all, the Winchesters were not particularly fond of Hellhounds.

**Notes for the Chapter:**

> An ending where the Winchesters gain a guardian 'Angel' in the form of an unlikely source ;)


	4. Snap

Castiel remembers the exact moment that his heart snapped in two. 

It wasn’t when he confessed his love to Dean, only to be snatched away from happiness by endless _nothing_. 

It wasn’t when he was yanked out of The Empty, only to witness Dean being impaled on a rebar. 

It wasn’t when he watched Sam grieve for his dead brother for decades before finally drifting off into an eternal slumber, his son by his side. 

No, Castiel’s heart was broken after all of this – in Heaven, actually.

It was a nice day. There were no _bad_ days in Heaven, because Jack and Castiel had made it that way. 

Souls greeted each other enthusiastically in their new resting place and Heaven was full of love and life in a way it had never been before. There were no more doors; no more ‘rooms’ for lonely souls to spend the rest of eternity in, reliving the same old memories over and over. 

This new Heaven was bright and exciting and brought truth to the whole ‘life after death’ theory. Even the recently-resurrected Angels thought so. 

Castiel had observed Dean’s passage to Heaven. He had watched the man greet long-dead family and he had smiled when Dean took Baby for a drive. His smile had widened when the two brothers had their reunion on an empty bridge and his heart had been bursting with love for the two humans that he considered family. 

He had waited patiently for them to seek him out and he was rewarded with Sam’s magnificent grin when the younger Winchester finally found him. He laughed as he was swept into a bone-crushing hug and he pretended not to notice the tears rolling down Sam’s cheeks for the sake of the human’s dignity. He hugged back tightly and ignored his own wet eyes. 

Finally, Sam left and Castiel waited for Dean.

And waited. 

And waited.

After a week had passed, Castiel’s patience had worn itself thin and he could no longer choke down the urge to see the man he had sacrificed everything for. He had planned on giving Dean time to come to terms with everything that had happened; everything that had been _said_. He had planned on letting Dean approach him first once he gathered enough courage to do so. 

Most of Castiel’s plans never came to fruition.

So, he flew to Dean with a warm grin and a heart filled with love, and he watched Dean startle at his approach. 

“Cas?” Dean asked tentatively.

Castiel’s eyes crinkled. “Hello, Dean.” 

They were alone, beside a gently-flowing creek, surrounded by tall pines and grassland, and Dean was perched in a camping chair, a fishing rod bobbing gently in his hands. 

Dean looked surprised.

“It’s good to see you,” Castiel said earnestly and Dean nodded slowly before standing. 

“…You too.”

The odd tone prompted Castiel’s brows to pinch for a moment before they smoothed out into a light smile as he took a step towards Dean. 

“How have you been?” Castiel asked softly, gesturing to the picture-perfect landscape.

Dean definitely looked nervous. “Uh… good, yeah. Happy.” He rolled his shoulders and didn’t quite meet Castiel’s gaze. 

Castiel held back a chuckle and took another step towards the most amazing human he had ever met.

“I apologise for how I left things between us,” he said quietly. “That wasn’t exactly how I planned to tell you.” 

Dean shifted his weight from one foot to the other. “Don’t… don’t worry, man. Forget about it.”

“No, Dean…” Castiel began as he shook his head. “You deserve better. Better than a rushed ‘goodbye’ and a rather rough shove into a wall.” 

“Really, Cas,” Dean mumbled as he scratched at the back of his head, “don’t even think about it. Water under the bridge, right?” 

Castiel’s gaze softened. “You have always forgiven me, even when I least deserve it.” He edged closer to Dean.

Dean’s gaze slid to his right and then to his left, as though he was looking for something important. “Uh… yeah…” 

Finally, Castiel closed the distance between them and squeezed Dean’s arm reassuringly. “I meant what I said.”

Dean coughed quietly and refused to meet Castiel’s gaze. “Yeah… I know.” 

No longer able to retrain himself around this human that he had _pined_ for over the past ten years, Castiel raised a hand to cup Dean’s cheek. They were finally free of Chuck’s plans; freed from the manipulations of Angels and the contorted lies of Demons; free to be whomever they pleased. 

_With_ whomever they pleased.

It didn’t matter that Dean couldn’t say the words back. It didn’t matter that he didn’t sweep Castiel into a tear-filled embrace. It didn’t matter that Dean wasn’t being all that articulate. 

They were here, together, exactly where they were meant to be.

“I love you so much,” Castiel whispered, the words tumbling from his lips without him telling them to. An invisible weight lifted from his chest and suddenly, he could breathe. Everything felt _so right_. 

Until it _didn’t_.

Dean tore away from him with a wide-eyed look and he once again shifted his gaze to the distant horizon, as though… as though… 

…As though he was searching for an escape route.

Castiel’s hand fell limp against his side as Dean began to shuffle his feet awkwardly. 

“Cas, I… man, you know you’re my best friend. I love spending time with you and I’m _so_ glad that you’re… that you’re okay. I really am.” He dragged his eyes to meet Castiel’s. “But I… I just…” 

Castiel’s throat dried and he felt a new, far heavier weight settle inside his chest.

“But you don’t… reciprocate,” Castiel whispered as the epiphany struck. 

Dean hesitated for a moment before shaking his head, guilt seeping into his gaze. “…I’m so sorry, man.”

 _Snap._

Castiel backed away as though struck. “No, I… I should be the one to apologise. I… I shouldn’t have assumed…” His tongue grew thick in his mouth and the words died before they reached his lips. It suddenly made sense why Dean hadn’t sought him out in this place. 

“I… I should go,” Castiel managed as he readied himself for a speedy exit.

“Wait, Cas,” Dean protested. “Don’t… We can still be friends, y’know?” 

Castiel shook his head rapidly, cheeks burning. He couldn’t think with the terrible roaring between his ears. “I need… I can’t…” His wings burst from his back. “I’m so sorry.” 

“Cas, wait!” Dean yelled as Castiel vanished. “Don’t do this!”

Castiel reappeared in the corridors of Heaven. He fell against a white wall and slid down it in anguish as a memory of his sacrifice resurfaced. 

_I love you._

_Cas… don’t do this._

The phrase took on a whole new meaning; the plea hadn’t been Dean begging him to stay, as Castiel had originally assumed. 

Dean hadn’t wanted to deal with Castiel’s feelings for him.

Castiel’s head plunged into his hands as his breaths shook. 

Why did nothing ever go to plan?

**Notes for the Chapter:**

> Whoops... my hand _slipped_ ;)
> 
> The finale could have been worse, right?
> 
> ...Right?


	5. Defeat

Michael flinched as Castiel was ripped from the Earth and plunged into The Empty. Another frequency from Angel Radio fizzled out, leaving nothing but white noise. There weren’t many channels left now. 

_Are you alright?_

Michael closed his eyes, focusing on the voice inside his head. “No,” he admitted softly. 

_I’m sorry. You don’t deserve this._

Michael sighed and leaned heavily against the wall. “I’m ninety percent certain that I do. I’ve done terrible things.” 

_You don’t._

A smile touched Michael’s lips. Adam had been his rock this past decade; a lifesaver for a drowning man. He hadn’t realised just how much he had spiralled since Lucifer’s fall and he had been so determined to bring the apocalypse to fruition that he hadn’t noticed just how much he had strayed from the path of Good; from his father’s path. 

He winced. His father was currently destroying the world because he was bored. Frustrated. Throwing a tantrum because his _toys_ wouldn’t do what he wanted them to. 

“You have too much faith in me,” Michael said quietly, glancing around the old barn. He swept his fingers over the rebar, eyebrows pinching together as the rust began to peel. 

_I trust you. I know you’ll do the right thing._

Michael curled his fingers around the rebar, letting its coolness seep into his skin. Human sensation was still foreign to him, but it was strangely pleasant. 

“You definitely have too much faith in me.”

Adam chuckled inside his head and Michael’s smile wormed its way back into his expression. Adam’s happiness had always touched his grace, infecting it with warmth and light until Michael had no choice but to succumb to its embrace. 

_You are good, even if you don’t always think so. Remember, I can see your grace._

Michael’s gaze softened as his hand slipped off the rebar. “How could I forget?” He pulsed warmth and appreciation into Adam’s soul and was rewarded with a burst of joy and amusement. “I don’t know what I’d do without you. You’ve kept me sane these past few years.” 

Inside his mind, Adam seemed to grin. _I’m not too bad for a second choice, then?_

Michael rolled his eyes at the old joke. “You have your drawbacks,” he teased as he rolled his shoulders. “Not quite as roomy as Dean.” 

_Shut your mouth. You wouldn’t have had nearly as much fun with Dean. Imagine the angst. The endless family issues. You’d probably still be in the cage with Lucifer right now. I, on the other hand, introduced you to toast and Game of Thrones._

Michael bit back a smile. “I do love burnt bread with my graphic violence and incest.”

 _Exactly._

A laugh escaped Michael’s throat before he could stop it and Adam’s soul brushed his grace affectionately.

 _You should laugh more often. Suits you._

Michael looked around the barn once more. He wasn’t entirely sure why he had come here, but when Atropos, Sister of Fate, had told him that this would be the place that Dean Winchester would die, he had been drawn towards it. After all, he had to see what kind of extraordinary venue would become the legendary Dean Winchester’s death bed. It had to be a phenomenal place, right? 

As it turned out, it was just a barn. A musty, abandoned barn with rotted walls and structural hazards such as exposed rebars. 

Dean Winchester would die, not in a blaze of glory, but upon a rusted piece of metalwork in the middle of nowhere, against monsters he had fought a thousand times before. Such a meaningless death. 

Michael eyed the rebar unhappily. “The universe has such a strange sense of humour.”

Silence. 

Michael frowned, immediately sensing something _wrong_. “Adam?”

More silence. 

Michael’s scowl deepened and he prodded at Adam’s soul only to find it absent. His eyes widened and he searched frantically through the recesses of his own mind, panicking when it proved devoid of Adam’s light. 

“Adam,” he said frantically, looking about himself in a useless manner. “Adam, where are you?”

No response. 

Michael’s grace trembled erratically as he staggered backwards. The emptiness was _horrifying_ after so many years of having the human’s soul pressed beside his grace, and a dreadful pit began to form in his stomach. This couldn’t be happening. 

“Adam, please!” Michael begged, clutching his chest as his human heart clenched tight enough to shatter. He felt as though he was about to break – as though he was being dragged deeper and deeper into a void of nothingness. There was too much weight on his chest, too much pressure in his too-human lungs… this was it. He was going to die. 

His back hit the wall and he slid down it, barely noticing that he was hyperventilating despite not needing to breathe. Deep in his grace, he knew what had happened. 

His father had taken Adam from him.

At first, he screamed out in anguish, digging his nails into the rotting wooden floors. He screamed and screamed, begging his father to bring Adam back. 

Then, he wrapped his arms around his legs and let his head fall against his knees as tears slithered down his cheeks. He cried silently, grace contorting painfully in defeat. He had lost _everything_ that had ever meant anything to him; his brothers and sisters, his father’s love, and now Adam. 

He had no reason to continue existing. He could fade away and no one would notice, no one would care.

He should stay here until his father ended everything. It would be less painful than attempting to move. 

…No.

No, that wasn’t right. 

Michael scowled as he sat upright again. He couldn’t give up – Adam deserved better. Adam had _faith_ in him.

Michael clenched his fists angrily and flicked his gaze Heavenward. No. This was not how he died. 

He was powerful. He could do _good_ , like Adam believed he would.

Slowly, he rose to his feet. The Winchesters and Castiel had brought one another back from the dead a hundred times; the least Michael could do was _try_ for Adam. 

He threw his wings out furiously as he narrowed his eyes. This was not how Adam died. He wouldn’t let Chuck take him away. 

He would not give Chuck the satisfaction of _winning_.

He would team up with the Winchesters, he would help them defeat Chuck, and if he had to pretend that he craved his father’s love and praise in order to trick him into bringing Adam back, then he would do so. He would do _anything_ for Adam, even if he had to swallow his pride and toss away his dignity. He was Adam’s angel and he would raise the human from perdition, no matter the cost to himself. 

And if he happened to save the Earth as he did so, well, that was just a bonus.

He shook out his wings, ready to take flight and head towards the bunker, but something caught his attention from the corner of his eye. 

He turned to the rebar slowly and stalked towards it. He smoothed his fingers over its tetanus-riddled surface before gripping it tightly and snapping it clean off the post. Then, he squeezed and it turned to dust beneath his palm. 

Smirking bitterly, he took flight.

Chuck had started a war and Michael would ensure that he was thoroughly defeated.

**Notes for the Chapter:**

> I've always had a bit of a soft spot for Michael ;) What if he 'betrayed' the Winchesters to bring Adam back (and maybe messed up the CW's plan to kill Dean off in the process)? Heck, he'd probably bring Cas back too ;)


	6. Epiphany

Dean wasn’t sure how long he spent crumpled against that wall, tears creeping down his cheeks as Cas’ words replayed over and over in his mind like a broken record. He didn’t know how many times Sam and Jack had frantically tried to call him, nor how many times his voicemail had answered them. He didn’t know how many times he had sobbed Cas’ name into the empty room. 

He closed his eyes, head pressed against his knees. His tears had long since dried up and his throat was raw and painful.

Cas was dead. 

He was dead because of Dean – because he had seen no other way to save the human he was in love with.

Dean’s breaths hitched violently and a pathetic noise spilled from his lips. Cas was _in love_ _with him_. 

_Had been_ in love with him. Past tense. Because he was dead.

Dean’s stomach jerked and he doubled over and dry-heaved. It seemed that his body had nothing left to give in the wake of his agonising grief. He dragged himself upright and collapsed against the wall again, breaths trembling from the effort. Everything felt so _wrong_. 

He hadn’t responded to Cas’ heartfelt speech; had barely reacted at all, really. Cas had died not knowing if Dean returned his feelings, or even _accepted_ them, because Dean had been too shocked to process what was happening around them and what Cas was telling him. 

Dean dragged a hand through his hair and sucked in a breath. He should have said something, should have replied, should have begged Cas to _stop_. Cas wouldn’t have listened, but he should have said _anything_ to make Cas understand that he… that he lo- 

The end to that train of thought was like a kick to the stomach and another broken sob was punched out of Dean.

How hadn’t he realised? 

“Come back,” Dean whispered into his knees as he curled into a ball. “Please, come back.”

He didn’t know how long he remained slumped against that wall, and he began to tremble as the unforgiving concrete leeched the warmth from his skin. 

Eventually, he took to staring despondently at the chipped floor, the light from his eyes dimming with every passing second. He was so _tired._

And then, he got angry.

 _Screw Chuck._

He suddenly surged to his feet and slammed his fist against the wall, uncaring of his protesting knuckles. He imagined Chuck’s face in place of the hard concrete and he grit his teeth furiously as he kicked at it for good measure. He flexed his hand and looked about the room with a deep scowl. 

“You know what? Screw you too, Cas,” Dean hissed at the spot Cas had been swallowed by The Empty. “Screw you for leaving! Screw you for being a martyr! Screw you for waiting until the last damn minute to tell me _that_!” 

He began to pace around the room like a trapped tiger, kicking debris as he went. “Why didn’t you tell me sooner?” he snarled at a ruined book as he gave it a vicious kick. “Why’d you just let it take you? We could have worked something out, just like we always do. No one had to die! _You_ didn’t have to die!” 

He grabbed a chair and hurled it against a wall before throwing his arms out and glaring at the spot Cas had disappeared from. “I’m so _sick_ of you sacrificing yourself for me and Sam. I’m _tired_ of you always getting a raw deal! Why can’t you just be selfish for once, huh? Why can’t you just look after yourself instead of trying so hard to take care of us?” 

Dean came to a halt, his voice taking on a certain gruffness in a mockery of Cas’ own tones. _“Happiness isn’t in the having. It’s in just being. It’s in just saying it.”_ Dean scoffed and glared at the same spot. “You could have had it if you hadn’t thrown yourself into The Empty! I would have given it to you!” he yelled, fists clenched. 

He began to tremble, chest throbbing. “Why didn’t you tell me about your deal? Why didn’t you tell me that you’d traded your life for Jack’s? We could have figured it out!” He snatched a broken chair leg from the floor and lobbed it into the wall. “You deserve more than this!” 

His body slumped and he inhaled a painful breath, heart nearly torn in half. “I need you here, Cas. I… I could have given you what you wanted if you’d have just _stayed_.” 

He rubbed his hands over his eyes as the anger and violence drained from each and every vein in his body. His mind cleared of thoughts and he stared dully at the destruction around him. 

“Are you always this dramatic?”

Dean snarled and whipped his gun from his pocket as he turned, firing three shots at Chuck’s chest. They merely glanced off him but the process of pulling the trigger on a being he despised so intensely brought him immense satisfaction. Chuck smiled in amusement and nudged the fallen bullet with his toe. 

“Bring him back,” Dean demanded.

Chuck’s smile widened. “No.” 

Dean fired another bullet between his eyes and Chuck caught it between two fingers.

“He doesn’t deserve this!” Dean yelled desperately. 

Chuck tossed the bullet onto the floor and thrust his hands into his pockets. “You just don’t get it, do you? It doesn’t matter what you think he deserves. In the end, your choices don’t matter. His choices don’t matter. I’m the author of your story.” 

“Then write him back into the book,” Dean hissed.

Chuck shook his head in mock disappointment. “Don’t you understand? This is the end. This is how it always ends. I’ve done all I can with Castiel’s story and when there’s nothing left to write, it’s time to let that character go. It’s been that way in all the other worlds.” Chuck’s gaze softened as a perverted smile twitched at his lips. “Castiel always dies. Sometimes after you, but most of the times, it’s before. In some worlds, he doesn’t even know who you are, but he _always_ dies. Just as you do.”

Chuck’s expression hardened and he took a step towards Dean. “Death is inescapable, Dean. For you and your brother. For Cas. You’ll die because I won’t allow your story to end any other way.”

Dean edged backwards, eying the door as an escape route. “You won’t win.”

“I already have,” said Chuck simply.

Dean shook his head angrily and focused on the despicable man before him. “Nah. You haven’t won. You’ve lost. Wanna know how I know that?” 

Chuck’s mouth drew into a thin, irritated line. “Enlighten me.”

“Because if you were winning, you wouldn’t be destroying your own creations. You wouldn’t have destroyed your sister. You wouldn’t be destroying everything you once loved in order to start again,” Dean smirked bitterly. “You’ve lost and you can’t stand to see your own failure, so you’re destroying everything that reminds you of the monster you’ve become.” He stared hard at Chuck. “Tell me I’m wrong.” 

Chuck squared his jaw and straightened. “I’m starting again because I’m _bored_ with you.”

Dean snorted. “If you were bored, you wouldn’t be dragging this out. You’d have killed me and Sam already. No, you’re not bored. You’re frustrated because things aren’t going according to your little script. You’re _losing_ and you can’t stand it. You failed.” 

Chuck took a step towards Dean, eyes narrowed. He pointed an accusing finger at Dean. “That’s not true. I’m winning. You’ve lost _everything_ you’ve ever loved. Every _one_ you’ve ever loved.” He smiled as his hand fell to his side, shoulders rising into a shrug. “Just like I planned. Just like I _wrote_.” 

Dean felt as though he’d just been kicked in the ribs. He sucked in a sharp breath to lessen the pain, but it lingered and Chuck noticed his discomfort. He grinned. 

“What’s wrong, Dean? Case of heartache? Has all this,” he gestured to the ruins around them, “only just settled into that thick skull?” Chuck smirked and advanced on Dean. “You will die, Dean. You and your brother and Jack and everyone else. Your _boyfriend_ was only the beginning.” 

Dean felt as though his ribcage wasn’t big enough for his lungs. He tried to hide the way his breath hitched at the word ‘boyfriend’ and he frantically ignored the pain forming in the back of his skull. Why hadn’t he realised sooner? Why hadn’t Cas said anything? Why did it hurt _so much?_

“Why are you doing this?” Dean asked, voice soft and brimming with agony as he edged towards the door. “Why can’t you just forget about us and move on? Create something new and just leave us here? Why are you torturing us like this?” 

“Cleaning up,” Chuck said simply. “No point in keeping broken toys.” He glanced at the door and it slammed shut with an impressive _bang_. 

Dean startled and cast his gaze to it helplessly.

“Not done with you yet,” hummed Chuck, waggling a finger. “But don’t worry, I’m not going to kill you. Not yet, anyway. I want to chat.” 

Dean glowered at him, exhaustion creeping up his frame. Honestly, he didn’t want to fight anymore, but Cas had sacrificed himself to save Dean and the older Winchester would not allow that sacrifice to be in vain. 

“Spare me the small talk,” Dean bit out.

Chuck glanced at him sharply and Dean yelped as his legs suddenly gave out and a pressure forced him to remain seated on the damaged floor, cross-legged in front of Chuck like an obedient child. 

“Look, Dean. I’m giving you an out,” said Chuck solemnly. “The best possible course of action at this point is for you and your brother and Jack to die. You’ll go to Heaven, have a _wonderful_ time, and I’ll destroy everything whilst you’re up there. You won’t even know that you’ve ceased to exist.” 

He clasped his hands together. “Down here it’s all pain and loss and grief, but up there – what’s left of it anyway – you can live out your final hours in paradise before I bleach the entire canvas. It’s win-win for all of us.” 

Dean wrinkled his nose in disgust before a frown pinched his brows. “…Why would you give us an out?”

Irritation flicked across Chuck’s expression. “Just take the offer.” 

“No,” Dean said firmly, lifting his chin. “Why give us an out? Why not just wipe us from existence right now? Why wait?” 

Chuck shifted his weight from one foot to the other and narrowed his eyes. “Where’s the fun in that? Try to be less idiotic than your usual self – take the offer.” 

Dean shook his head, mind whirring. “You’ve not killed me and Sam for some reason and although Jack’s supposed to be a weapon against you, you’ve not killed him either, even though he’s weak.” Dean scowled as he wheedled through the information buzzing around his brain. “You didn’t kill Cas either – The Empty took him. Why would you ask us to take an offer like that unless… unless…” Dean’s gaze snapped up to meet Chuck’s glare. “Unless you _can’t_ kill us. Unless something’s stopping you.” 

Chuck ground his teeth together. “And what would be stopping me from wiping you from existence, hm? Surely, you’re not this stupid? I’m more powerful than _anything_ you’ve ever met before.” 

A grim smile pulled at Dean’s lips. “Nah, you’re on a time limit, aren’t you? Something is holding you back and you’re starting to sweat because if Jack’s powers return, you’re just another soon-to-be-dead monster.” 

“Enough,” growled Chuck, flinging a hand out to silence Dean. Pressure built around Dean’s throat, narrowing his airways slowly until he was gagging and clutching at the invisible rope around his neck. 

Suddenly, the pressure seemed to… flicker, and then it disappeared entirely and Dean was allowed to breathe. Chuck clenched his fist. 

“Stop interfering!” he snarled.

Dean jerked in surprise before the epiphany struck. 

“Amara,” Dean whispered before smirking. “She’s holding you back, isn’t she?”

Chuck shot him a withering glare. “She’s annoyingly fond of you.” 

Finding that he was no longer bound to the floor, Dean stood slowly. “You tried to absorb her power and now she’s not happy with you,” Dean said, a grin taking over his face. “You tricked her.” 

“So did you,” Chuck hissed.

“Yeah, but we were right about you, weren’t we? And now, she can see that. She’s on our side.” For the first time in weeks, Dean felt a glimmer of hope. 

“She won’t be able to protect you for long,” Chuck said coldly. “She’s getting weaker from fighting me.”

“All she has to do is give us a little more time,” Dean shot back before heading towards the door and leaving Chuck standing in the centre of the room, knuckles white. “We’re gonna beat you. All of us, together.”

He paused in the door frame and turned to Chuck with a growl. “And I’m getting my angel back, one way or another.”

“The Empty won’t let you,” spat Chuck. 

“Then I’ll make an offer it can’t refuse,” Dean snarled fiercely. “His life for yours.”

Chuck’s eyes widened and Dean grinned. “Yeah, I imagine you’re not in its good books after yanking Lilith out of the void. Heck, who knows how many angels and demons you’ve stolen from it? How many times you’ve _disturbed its sleep?_ I’ll bet that it would love to get its claws on you.” 

Chuck was starting to look nervous and Dean’s eyes brightened with amusement. “All I need to do is figure out how to summon it and Jack won’t even have to lift a finger to kill you. None of us will. The Empty will do it for us.” 

Chuck snapped his fingers and vanished.

Dean snatched up his phone and raced out of the bunker in search of Sam and Jack.

* * *

Castiel opened his eyes to find Meg standing over him.

No, not Meg. The Shadow.

He frowned at it in confusion, wondering why he had been woken up from eternal nothing. 

“A new arrangement has been made,” said The Shadow with a wicked smile.

Castiel’s eyes widened as The Shadow pressed two fingers against his temple. 

Everything went white.

**Notes for the Chapter:**

> _LuckyFlucky_ and I agreed that Amara switching sides was a terrible plot device. 
> 
> So I switched her back ;)


	7. Komorebi

Sunlight filtered through the trees, bathing the Impala’s glossy finish in speckles of flickering orange hues. As the sun fell lower, Dean closed his eyes, allowing the delicate patches of light to flutter over his body, warmth lingering at every point they touched. 

“Komorebi,” Dean announced as the Impala’s hood dipped with the weight of the person settling beside him.

His companion turned to him in query. 

“Komorebi,” Dean said again, gesturing towards the thick forest ahead of them. “It’s Japanese. Describes the way sunlight shines through trees.” 

The person beside him gazed curiously at the light-spattered flora.

Dean placed his hands together over his lap and smiled as his eyes remained shut. “On Earth, I couldn’t even speak Spanish. Now I can speak _everything_.” 

“You’re enjoying Heaven, then?” asked a familiar voice that made Dean’s smile widen.

“Yeah. Whoever kicked this place into shape did good. Real good. Amazing, actually.” He opened his eyes to stare into the forest once more as the sun sunk lower and the sky began to fade to a reddish-umber. 

“…I’m glad you approve.”

Dean spared Castiel a grin before casting his gaze to the trees once more. The speckles of light were beginning to retreat from Dean’s boots on a slow journey towards the forest. 

“Y yo a ti,” Dean said after a long moment.

Beside him, Castiel frowned in confusion and swivelled his head with a cocked eyebrow. “Excuse me?” 

Dean’s lips twitched in amusement as he glanced at Castiel. “Y yo a ti,” he repeated.

Castiel shook his head minutely, at a loss, so Dean turned to him fully. 

“Te quiero con todo mi corazón,” Dean hummed.

Castiel blinked, then his eyes widened, so Dean continued. 

“T’es l’amour de ma vie,” he whispered, a grin tugging at his lips.

Castiel’s eyes were round as his mouth flopped open, words never breaking out of his throat. 

“Du bist mein Ein und Alles,” Dean said sincerely with a terrible German accent; Heaven allowed him to understand the languages, but it didn’t grant him the perfect tongue with which to _speak_ them. 

Castiel was openly gaping at him, looking both confused and horrified. This would have been a blow to Dean’s confidence had the Angel not literally _died_ for him – his last choked words being ‘I love you’. 

“Senza di te la vita non ha più senso,” Dean whispered, fully enjoying himself.

Castiel looked rather constipated. “Dean-” he began before cutting himself off, eyes glistening with what appeared to be confusion and despair. 

That wouldn’t do.

Sliding his hand across the sun-warmed hood, Dean’s fingers closed over the Angel’s. He decided to speak plainly. 

“I love you too,” he offered softly, squeezing Castiel’s hand and wondering when it had begun shaking.

Castiel tensed for a moment, looking caught-out, but after a minute had ticked by and Dean hadn’t withdrawn his hand, Castiel started to relax little-by-little and his eyes brightened. 

“…You… do?” he asked tentatively.

Dean forced his smile not to dim. How long had Castiel been hiding his feelings? How long had Dean been oblivious to them? 

“Yes,” he said firmly, so there would be no more misunderstandings between them. He held Castiel’s hand tighter. “I must really suck at showing it if you don’t believe me.” 

Castiel opened his mouth, then immediately snapped it shut, looking torn. “…Maybe a little?”

A laugh of disbelief erupted from Dean’s throat as he stared at the Angel. “Hey, I just poured my heart out to you! You’re not supposed to agree that I suck!” 

A smile pulled at Castiel’s lips. “Well, it did take me dying for you… _again_ …”

Dean laughed warmly this time before slinging an arm around Castiel and hauling him into his side. The car rocked and groaned and Castiel looked startled at first, but he quickly sagged against Dean – the sort of full body sag that Dean had never seen before; a sag filled with relief and hope and contentedness. 

Castiel leaned into Dean with a shaky breath and Dean rested his head against the Angel’s. “Yeah… you have to stop doing that.” 

Closing his eyes, Castiel smiled and allowed Dean to hold him. “I was afraid you wouldn’t want to see me after… well, after everything. I realise that my timing was… suboptimal,” he confessed softly. 

A frown pinched Dean’s brows. “Is that why you didn’t come to see me at first? We’re you afraid I’d, ah… say _no_?”

Castiel gave an almost imperceptible nod, refusing to meet Dean’s gaze. “I didn’t say any of that to hear it back from you. I believed it would be the end for me and I… I wanted you to know.” He cleared his throat quietly. “I just… didn’t expect to be brought back.” 

Dean carefully pressed his nose into Castiel’s hair. “I’m glad you were,” he whispered, lips brushing the Angel’s ear in a feather-light caress. “I missed you. I thought you were… gone.” 

Castiel turned slowly until their foreheads rested against one another and they could feel the heat of each other’s breaths on their faces.

“I’m here now,” Castiel promised quietly.

A moment of silence passed between them before Dean tilted his head and ghosted his lips across Castiel’s. He began to draw back, but Castiel’s lips chased his and he slumped a little as a soft mouth moulded lightly against his own. Dean found himself wanting to tug Castiel closer as the Angel pulled away to gaze at him. 

The corners of Castiel’s eyes crinkled with joy and Dean grinned back fondly before pulling the Angel into his side once more and returning his gaze to the picturesque sunset. A dark head fell against his shoulder and a gentle sigh tumbled over Castiel’s lips. 

“You have no idea how long I’ve wanted to do that.”

“You should have said something sooner,” Dean murmured. “Perhaps things would’ve been different.” 

Castiel shifted into him. “I liked the way things were.” A pause. “Besides, if I had said something sooner, Sam and I would have had to deal with you and your gay panic for at least two months. It would have been exhausting.” 

Dean snorted and slapped Castiel’s arm in mock scolding. “I wouldn’t have had a ‘gay panic’.”

“You’d have added ‘no homo’ to the end of every conversation,” Castiel said solemnly. 

“I wouldn’t have!”

“You’d have clarified that you liked me ‘platonically’ at least thirty-six times. You’d have probably called me ‘family’ seventeen times and then told me _‘You’re like a brother to me, Cas’_ eleven times,” Castiel said, imitating Dean’s voice astonishingly well. 

“Shut up!” Dean laughed as a hint of a smile played about Castiel’s lips. “I wouldn’t have done that.”

“I know you, Dean Winchester,” Castiel hummed. “I know exactly what you’re like, or did you forget that I pieced your soul back together before you even knew my name?” 

Dean flicked his eyes to Castiel with a softness that the Angel didn’t notice. He admired Castiel’s profile for a few moments; his ocean eyes, the curve to his lips, the beginnings of stubble lining his jaw… His own Guardian Angel. He would never forget _anything_ that Castiel had done for him. 

“That’s true. I suppose that when you had that date with April, I did ask you to ‘lose the vest’ and ‘unbutton your shirt’ _platonically_. And all those times I _platonically_ stared into your eyes from across the room. Oh, and that time I _platonically_ searched literally all of purgatory for you because I couldn’t stand the thought of losing you.” He cocked an eyebrow at the wide-eyed Angel. “You want me to keep going?” 

Castiel spluttered for a moment, cheeks red, before he snapped his mouth shut and whipped his head around to face the forest. Dean smirked and squeezed his hip. 

“…Well, why didn’t you say anything?” Castiel asked petulantly.

It was Dean’s turn to find the forest _very_ interesting. “…Y’know,” Dean coughed and gesticulated vaguely. “Because… because I…” He snapped his mouth shut as Castiel began to smirk triumphantly. “Oh, shut up,” he grumbled. 

“Straight as a rainbow,” Castiel muttered before Dean smacked his arm.

They settled against one another again and lapsed into a comfortable silence as the sun threatened to disappear below the horizon. Eventually, Castiel closed his eyes and basked in Dean’s warmth. 

“I was wrong,” he murmured and Dean cast him a curious glance.

“Happiness isn’t in just saying it,” Castiel clarified. “It’s not enough to just _say_ it. Not now. Not now that I know what it might be like to actually _have_ it.” He paused and glanced up at Dean. “To have _you_.” 

Dean smiled tenderly and pressed his lips to Castiel’s head. “…So, that thing you said you wanted but knew you couldn’t have…?”

“Turns out I may have been wrong,” Castiel chuckled quietly as he slipped an arm around Dean. “Although I’m still mad at you.”

Dean’s eyebrow’s shot skywards. “Why?”

Castiel pulled back to stare at him, unimpressed. “A rebar? Really?” 

Dean grimaced. “Accidents happen.”

Castiel narrowed his eyes. “You fight deadly monsters every day. You battled leviathans. You’ve been to Heaven, Hell, and Purgatory and _lived_ to tell the tale. You literally defeated God and I sacrificed my own life to save you from Death herself… and what finally finishes you off is an _overgrown_ _rusty nail_? You don’t even call an ambulance? Really, Dean?” 

Cheeks red, Dean dropped his gaze. “Sorry,” he mumbled.

“The funky taco was a better death!” 

“Ok, you can shut your mouth,” Dean huffed. “You weren’t even there for that one.”

Castiel was outright grinning. The _nerve_. “I’d yell at you for being careless if it wasn’t so hilarious.” 

“Alright, you know what?” Dean growled as he grabbed Castiel’s cheeks between his palms. “I’m gonna _make_ you shut up.” He suddenly swung his leg over Castiel’s lap and shoved the Angel back against the hood. 

Castiel’s eyes blew wide as his spine hit the warm metal and he stared up at Dean in surprise, before his smile widened as Dean set to work on his promise.

**Notes for the Chapter:**

> “Te quiero con todo mi corazón,” - I love you with all of my heart - Spanish  
> “T’es l’amour de ma vie,” - You're the love of my life - French  
> “Du bist mein Ein und Alles,” - You are my one and only - German  
> “Senza di te la vita non ha più senso,” - Without you, life has no meaning - Italian
> 
> \---  
> Ooo look. I made a fluffy one.


	8. Pie

**Notes for the Chapter:**

> Warning at bottom

“Are you sure you’re ready for this?”

_No._

“Oh, I don’t have a choice.” 

_How could he ever be ready? How could he keep going as though… as though nothing had happened? As though everything was all right. Normal. Happy._

“This is my destiny,” Dean said stoically. “It’s just so beautiful.”

 _Mask that pain with humour, like you always do. Maybe this time Sam won’t look at you with pity in that all-too-knowing gaze. Pretend that you’re fine. Pretend that everything is fine._

“Are you crying?”

“What? No.” 

_Better luck next time._

“I’m gonna go get some… uh…” Dean hesitated. _What was he supposed to say again? Something to distract Sam from looking at him like that. Something to distract himself from the empty feeling in his ribcage._

“…Pie?”

 _That was it._ “I’m gonna get some damn pie,” Dean agreed enthusiastically. _When would that hollow feeling fade?_

_Probably never._

He weaved through clusters of people. Civilians all going about their day as though they had no recollection of the past month; mostly because they didn’t. For them, nothing unusual had happened. Life continued. 

Dean closed his eyes for a moment and took a breath before opening them. He looked down at his lap and the assortment of pies gathered there. 

_Bury it all deep down, where no one would ever find it. Stuff those thoughts in a locked chest and throw away the key. Maybe one day, when he was old and grey and hooked up to a beeping machine, he would find that chest again and pick its lock. Perhaps he wouldn’t feel quite so numb then._

He flicked his gaze to Sam and found his brother staring morosely into space. “What? What’s wrong?”

Sam startled and graced Dean with a guilty glance. “Nothing. I’m fine.” 

_Why did Sam look so down? He had Eileen back. They had a dog running around the bunker like Sam had wanted since he was, what? Twelve? Their lives weren’t being controlled by Chuck anymore. What did Sam have to be upset about? Sam wasn’t the one whom had lost his best friend. Sam wasn’t walking around like an empty husk of himself. Sam hadn’t lost the angel he’d-_

“No, come on. I know that face,” Dean interrupted his own thoughts. “That’s, uh… that’s Sad Sam face.”

Sam looked mildly offended. “I’m not Sad Sam. I’m just…” His brows furrowed as though he was in pain; as though the following words physically wounded him. “I’m thinking about Cas, you know? Jack.” He swallowed and gazed blankly at his lap as Dean forced himself to breathe. 

“Wish they could be here,” Sam said softly.

“Yeah,” Dean murmured in agreement. He had a headache. And a stomach ache. “Yeah, no. I think about ‘em, too.” 

He shook his head and managed to meet Sam’s gaze. “You know what? That pain’s not gonna go away. Right?” _Right._ “But if we don’t keep living, then all that sacrifice is gonna be for nothing.” 

Cas’ _sacrifice will be for nothing._

“So, quit being a friggin’ Eeyore, huh?” _Please don’t make me talk about this, Sam. Not yet. Not ever. I just… I can’t. I can’t think about it. About them. About_ him _._

“Come on,” he said, gesturing to the box of pies. “Get into this.”

_Such a waste. If only things had gone differently. If he had his time over again. If he could go back to that moment…_

_Pointless thoughts. Can’t go back. Can’t change what has passed. Have to suffer with the consequences._

“Yeah, you’re right,” Sam sighed. 

_Of course he was. He’d not stopped thinking about what had happened for the past month. Everything was wrong and there was nothing he could do to fix it. He was a broken man and there was no angel there to heal him._

A pie crashed into his face. He might have been genuinely annoyed if he had the capacity to feel anything but anguish and numbness. 

“I have wanted to do that for a very long time,” Sam said, a smile on his face that didn’t quite reach his eyes.

Dean swiped a finger across the mess on his face, putting on a show for his brother. He had to at least try to be normal even if he was crumbling on the inside. 

He stuck his finger in his mouth, sucked it clean, and promptly passed out.

* * *

“Everybody’s gonna die, Cas, _everybody._ ” Dean stared at the floor as waves of helplessness swept over him, dragging him under, drowning him. “I can’t stop it.” 

Castiel looked no brighter. He turned to the door and a rune ignited upon its surface in fiery orange.

“She’s gonna get through that door,” Dean said miserably. 

“I know,” Castiel responded, equally as miserable.

“And she’s gonna kill you, and then she’s gonna kill me,” Dean continued wretchedly. Castiel spared him a brief, sorrowful glance and Dean’s whole body _ached_. 

“I’m sorry,” he whispered as Castiel turned away in defeat.

Then, Castiel’s expression changed and he slowly returned his gaze to Dean. “Wait, there is… there’s one thing she’s afraid of. There’s one thing strong enough to stop her.” 

Dean raised his eyes to meet Castiel’s, daring to hope that the angel had one more trick up his sleeve; that he would save the day just as he had so many times before. 

“When Jack was dying, I… I made a deal to save him.”

Alarm bells blared in Dean’s mind. “You _what?”_

“The… the price was my life,” Castiel continued as though Dean hadn’t spoken, and Dean’s stomach contorted with an overwhelming feeling of _wrongness_. “When I experienced a moment of true happiness, the Empty would be summoned and it would take me, forever.” 

Dean frowned. There was something… strange niggling at the back of his mind. Something insistent, as though it was trying to remind him of something. “Why are you telling me this now?” 

“I always wondered,” Castiel ploughed on, ignoring Dean once again, “ever since I took that burden, that _curse_ , I wondered what it could be, what… what my true happiness could even look like. I never found an answer.” He managed a weak smile. “Because the one thing I want… it’s something I know I can’t have.” 

_You can._

Dean startled at the stray thought. Where had that come from? What did it mean? He wasn’t even sure what Cas was talking about so why would the little voice in his head say that? 

“But I think I know… I think I know now,” Castiel said softly, as though he hadn’t noticed Dean’s confused frown. “Happiness isn’t in the having. It’s in just being. It’s in just saying it.” 

Dean shook his head slightly. Cas had… they’d had this conversation before, hadn’t they? Or maybe something similar? Perhaps it had been a dream. 

“What are you talking about, man?”

“I know how you see yourself, Dean. You see yourself the same way our enemies see you,” Castiel said, determination filling his voice in an eerily familiar way. “You’re destructive and you’re angry and you’re broken. You’re… you’re _‘Daddy’s Blunt Instrument’_. And you think that hate and anger, that’s… that’s what drives you. That’s who you are.” 

Castiel lifted his chin, eyes wide and pleading and filled with _so much_ desperation and anguish. _“It’s not,”_ he said fiercely. “And everyone who knows you sees it. Everything you have ever done, the good and the bad, you have done for love. You raised your little brother for love. You fought for this whole world for love. _That_ is who you are. You’re the most caring man on Earth. You are the most selfless, loving human being I will ever know.” 

There was a tightness in Dean’s chest and a burning sense of déjà vu at the back of his mind. Had he… had he heard this before? He couldn’t have. He needed to focus. Cas was leading to something important; he could feel it. 

“You know,” Castiel said with a bitter sort of smile, “ever since we met and ever since I pulled you out of Hell, knowing you has changed me. Because you cared, I cared. I cared about you. I cared about Sam. I cared about Jack. I cared about the whole world because of _you_. You changed me, Dean.” 

Dean’s pulse began to race. Why was this all so familiar? The bunker, the rune, Billie, Cas… “Why does this sound like a goodbye?” 

Castiel’s face crumpled even as his mouth curved into a sad smile. “Because it is.”

Dean’s eyes widened and the voice at the back of his mind screamed in frustration for him to _remember_. 

“I love you,” said Castiel.

 _DO SOMETHING, NOW!_

“Don’t do this, Cas,” Dean begged, blocking out the voice.

There was a horrendous wet noise behind Dean and he turned slowly, already guessing what he was about to see despite never having come into contact with the Empty before. Before he even got a chance to take in the sight of black goo oozing out of the wall, Billie kicked the door open with a furious glower. 

“Cas,” Dean said in alarm as Castiel reached forward and placed a hand on his shoulder.

“Goodbye, Dean.” 

“What?” Dean managed before he was hurled against the wall.

He lay there for a moment and watched as two oozing, sludgy limbs fired out of the dripping mess swirling over the adjacent wall. One curled around Billie as the other practically swallowed Castiel, and Dean’s breath hitched because he _had_ seen this before and this was the end and Cas was about to _die_ and he would have to carry on as though nothing had happened, as though Castiel hadn’t just poured his heart out to him, fully expecting Dean to reject him. _The one thing I want… it’s something I know I can’t have._

It suddenly made sense.

“Cas!” Dean screamed as he stumbled to his feet and made to grab Castiel. 

_Too late._

Dean watched as Cas _dissolved_ beneath a black, gooey limb and bile rose up his throat as the angel was sucked into the roiling nothingness. 

His legs gave out and he collapsed to the floor in the wake of familiar silence. Castiel was gone. Again.

He had been here before. He had seen all of it before – whether he had experienced a vision or a premonition, he wasn’t sure – but he had been gifted a second chance. 

And he had done nothing.

Tears shimmered in his eyes and he swiped at them angrily before running a hand through his hair. 

Cas was wrong. Dean _was_ broken. He had been given the chance to change things, to save the angel and he had failed.

He let his head sink into his hands and cried silently.

* * *

They defeated Chuck eventually but somehow lost Jack. Throughout it all, Dean was hit with the same feelings of familiarity and numbness and when he arrived at the pie festival, he was even less enthusiastic than the first time he vaguely remembered being there… or maybe _dreamed_ being there. 

Sam looked more concerned than he remembered and once again, Dean ignored the pitying looks and tried not to think too hard about Castiel as he settled down with his assortment of pies.

He flicked his gaze to Sam and found his brother staring morosely into space. “What? What’s wrong?”

Sam startled and graced Dean with a guilty glance. “Nothing. I’m fine.”

_Why did Sam look so down? He had Eileen back. They had a dog running around the bunker like Sam had wanted since he was, what? Twelve? Their lives weren’t being controlled by Chuck anymore. What did Sam have to be upset about? Sam wasn’t the one whom had lost his best friend. Sam wasn’t walking around like an empty husk of himself. Sam hadn’t lost the angel he’d-_

He’d had those thoughts before, hadn’t he?

“No, come on. I know that face,” Dean interrupted his own spiralling insanity. “That’s, uh… that’s Sad Sam face.”

Sam looked mildly offended. “I’m not Sad Sam. I’m just…” His brows furrowed as though he was in pain; as though the following words physically wounded him. “I’m thinking about Cas, you know? Jack.” He swallowed and gazed blankly at his lap as Dean forced himself to breathe. 

“Wish they could be here,” Sam said softly.

“Yeah,” Dean murmured in agreement. He had a headache. And a stomach ache. And he was pretty sure that he’d had this conversation before. “Yeah, no. I think about ‘em, too.” 

He shook his head and managed to meet Sam’s gaze. “You know what? That pain’s not gonna go away. Right?” _Right._ “But if we don’t keep living, then all that sacrifice is gonna be for nothing.” 

Cas’ _sacrifice will be for nothing. Again._

“So, quit being a friggin’ Eeyore, huh?” _Please don’t make me talk about this, Sam. Not yet. Not ever. I just… I can’t. I can’t think about it. About them. About_ him _._

“Come on,” he said, gesturing to the box of pies. “Get into this.”

_Such a waste. If only things had gone differently. If he had his time over again. If he could go back to that moment…_

_Pointless thoughts. Can’t go back. Can’t change what has passed. Have to suffer with the consequences._

_But he had gone back, hadn’t he? Or he’d had a premonition and then the events had played out exactly as he had dreamed them. It hadn’t changed anything. He was still an angel short._

“Yeah, you’re right,” Sam sighed.

 _Of course he was. He’d not stopped thinking about what had happened for the past month. Everything was wrong and he had done nothing to fix it when he was given the opportunity. He was a broken man and there was no angel there to heal him._

A pie crashed into his face. He might have been genuinely annoyed if he had the capacity to feel anything but anguish and numbness and a mocking sense of familiarity. 

“I have wanted to do that for a very long time,” Sam said, a smile on his face that didn’t quite reach his eyes.

Dean swiped a finger across the mess on his face, putting on a show for his brother. He had to at least try to be normal even if he was crumbling on the inside. 

He stuck his finger in his mouth, sucked it clean, and everything went black.

* * *

“Everybody’s gonna die, Cas, _everybody._ ” Dean stared at the floor as waves of helplessness swept over him, dragging him under, drowning him. “I can’t stop it.” 

Castiel looked no brighter. He turned to the door and a rune ignited upon its surface in fiery orange.

“She’s gonna get through that door,” Dean said miserably. 

“I know,” Castiel responded, equally as miserable.

“And she’s gonna kill you, and then she’s gonna kill me,” Dean continued wretchedly. Castiel spared him a brief, sorrowful glance and Dean’s whole body _ached_. 

“I’m sorry,” he whispered as Castiel turned away in defeat.

Then, Castiel’s expression changed and he slowly returned his gaze to Dean. “Wait, there is… there’s one thing she’s afraid of. There’s one thing strong enough to stop her.” 

Dean raised his eyes to meet Castiel’s, daring to hope that the angel had one more trick up his sleeve; that he would save the day just as he had so many times before. 

_Wait._

_Hadn’t they done this before? Hadn’t they been here before?_

“When Jack was dying, I… I made a deal to save him.”

Alarm bells blared in Dean’s mind, and not only because of the atrocity Cas had just admitted to. “You _what?”_

_The price was Cas’ life. That’s what he was going to say._

“The… the price was my life,” Castiel continued as though Dean hadn’t spoken, and Dean’s stomach contorted with an overwhelming feeling of _wrongness_. “When I experienced a moment of true happiness, the Empty would be summoned and it would take me, forever.” 

Dean frowned. He had been here twice before. They’d had this conversation before. The problem was that Dean couldn’t quite remember how it ended. Why was he experiencing such strong déjà vu? “Why are you telling me this now?” 

“I always wondered,” Castiel ploughed on, ignoring Dean once again, “ever since I took that burden, that _curse_ , I wondered what it could be, what… what my true happiness could even look like. I never found an answer.” He managed a weak smile. “Because the one thing I want… it’s something I know I can’t have.” 

_You can._

Dean startled at the stray thought. Where had that come from? What did it mean? What was he missing? 

“But I think I know… I think I know now,” Castiel said softly, as though he hadn’t noticed Dean’s confused frown. “Happiness isn’t in the having. It’s in just being. It’s in just saying it.” 

Dean shook his head slightly. “Have we… have we done this before?” he asked, tentatively.

Castiel’s brows furrowed in confusion. “I… I don’t…? Look, Dean, I know how you see yourself. You see yourself the same way our enemies see you,” Castiel said, determination filling his voice in an eerily familiar way. “You’re destructive and you’re angry and you’re broken. You’re… you’re _‘Daddy’s Blunt Instrument’_. And you think that hate and anger, that’s… that’s what drives you. That’s who you are.” 

Castiel lifted his chin, eyes wide and pleading and filled with _so much_ desperation and anguish. _“It’s not,”_ he said fiercely. “And everyone who knows you sees it. Everything you have ever done, the good and the bad, you have done for love. You raised your little brother for love. You fought for this whole world for love. _That_ is who you are. You’re the most caring man on Earth. You are the most selfless, loving human being I will ever know.” 

There was a tightness in Dean’s chest and a burning sense of déjà vu at the back of his mind. Cas was leading to something important; he could feel it. He could _almost_ remember it. 

“Are you _sure_ we haven’t done this before?” he asked, puzzled, because the bunker, the rune, Billie slamming her fists against the door, Cas pouring his heart out… every bit was _familiar._ Irritatingly so. 

Castiel raised his eyebrows in surprise and maybe an ounce of frustration. “You know,” Castiel said a little tighter than Dean remembered him speaking last time, “ever since we met and ever since I pulled you out of Hell, knowing you has changed me. Because you cared, I cared. I cared about you. I cared about Sam. I cared about Jack. I cared about the whole world because of _you_. You changed me, Dean.” 

Dean’s pulse began to race. “Why does this sound like a goodbye?”

Castiel’s face crumpled even as his mouth curved into a sad smile. “Because it is.” 

He had definitely been here before. They had been through it at least once, maybe twice, already?

“Don’t do this, Cas,” Dean begged, already guessing Cas’ next three words. 

“I love you,” said Castiel.

 _DO SOMETHING, NOW!_

“Wait a second-”

There was a horrendous wet noise behind Dean and he turned slowly, already guessing what he was about to see despite never having come into contact with the Empty before. Before he even got a chance to take in the sight of black goo oozing out of the wall, Billie kicked the door open with a furious glower. 

“Cas,” Dean said in alarm as Castiel reached forward and placed a hand on his shoulder. Dean stared at the hand as the epiphany struck. He had forgotten what Cas did next and there wasn’t enough time to stop him.

“Goodbye, Dean.”

“No, don’t!” Dean managed before he was hurled against the wall.

He lay there for a moment and watched as two oozing, sludgy limbs fired out of the dripping mess swirling over the adjacent wall. One curled around Billie as the other practically swallowed Castiel, and Dean’s breath hitched because he _had_ seen this before and this was the end and Cas was about to _die_ and he would have to carry on as though nothing had happened, as though Castiel hadn’t just poured his heart out to him, fully expecting Dean to reject him. _The one thing I want… it’s something I know I can’t have._

He had frozen _again_. Why hadn’t he said something? Why hadn’t he _done_ something?

“Cas!” Dean screamed as he stumbled to his feet and made to grab Castiel. 

_Too late._

Dean watched as Cas _dissolved_ beneath a black, gooey limb and bile rose up his throat as the angel was sucked into the roiling nothingness. 

His legs gave out and he collapsed to the floor in the wake of familiar silence. Castiel was gone.

 _No. Nononono._ How could he have failed _again?!_

Three chances to save the angel he loved and all of them _wasted_.

 _Crap_. Was that the first time he had admitted to himself that he…? 

The tears fell faster than last time and he curled into a ball and prayed for Cas to come back to him.

He didn’t.

* * *

Chuck was left alive as a human and Jack disappeared into the raindrops or _whatever_. Dean’s past couple of months had consisted of heavy drinking and disapproving looks from his brother. When he neared the pie festival, he was ready to keep driving, but Sam somehow convinced him to stop. 

He was no longer particularly interested in eating and the prospect of a box of pies was nauseating to him. He grabbed one slice to keep up appearances and to stop Sam’s damn pitying stare. It only marginally succeeded in distracting his brother.

He flicked his gaze to Sam and found his brother staring morosely into space. “What? What’s wrong?”

Sam startled and graced Dean with a guilty glance. “Nothing. I’m fine.”

_Why did Sam look so down? He had Eileen back. They had a dog running around the bunker like Sam had wanted since he was, what? Twelve? Their lives weren’t being controlled by Chuck anymore. What did Sam have to be upset about? Sam wasn’t the one whom had lost his best friend. Sam wasn’t walking around like an empty husk of himself._

_Sam wasn’t the one living a nightmare over and over._

“No, come on. I know that face,” Dean grumbled moodily as he pushed his pie around the flimsy paper plate. “That’s, uh… that’s Sad Sam face.”

Sam looked mildly offended. “I’m not Sad Sam. I’m just…” His brows furrowed as though he was in pain; as though the following words physically wounded him. “I’m thinking about Cas, you know? Jack.” He swallowed and gazed blankly at his lap as Dean forced himself not to sigh. _Sam was about to say that he wished they were there, wasn’t he?_

“Wish they could be here,” Sam said softly.

 _Ten points to Dean._ “Yeah. Me too.” _What else was he supposed to say? Oh yeah._ “You know what? That pain’s not gonna go away. Right? But if we don’t keep living, then all that sacrifice is gonna be for nothing. So, quit being a friggin’ Eeyore, huh?” _Please don’t make me talk about this, Sam. I’ve lived through it three times already._

“Here,” he sighed as he handed Sam the untouched pie. Sam stared at him with wide, horrified eyes.

_Such a waste. If only things had gone differently. If he had his time over again. If he could go back to that moment…_

_Pointless thoughts. Can’t go back. Can’t change what has passed. Have to suffer with the consequences._

_But he had gone back, hadn’t he? And he’d failed three times now. He was still an angel short. No. He never wanted to go back – he couldn’t watch Cas die again._

“Are you… are you feeling alright?” Sam asked carefully, staring at Dean’s head as though there was a second face attached to it.

_Not even close._

Dean rolled his eyes and, merely to shut his brother up, swiped his finger through the cream on top of the pie and shoved it into his mouth. 

The world tilted to the left and faded to black.

* * *

“Everybody’s gonna die, Cas, _everybody._ ” Dean stared at the floor as waves of helplessness swept over him, dragging him under, drowning him. “I can’t stop it.” 

Castiel looked no brighter. He turned to the door and a rune ignited upon its surface in fiery orange.

“She’s gonna get through that door,” Dean said miserably. 

“I know,” Castiel responded, equally as miserable.

“And she’s gonna kill you, and then she’s gonna kill me,” Dean continued wretchedly. Castiel spared him a brief, sorrowful glance and Dean’s whole body _ached_. 

“I’m sorry,” he whispered as Castiel turned away in defeat.

Then, Castiel’s expression changed and he slowly returned his gaze to Dean. “Wait, there is… there’s one thing she’s afraid of. There’s one thing strong enough to stop her.” 

Dean raised his eyes to meet Castiel’s, daring to hope that the angel had one more trick up his sleeve; that he would-

 _Wait a minute. He’d done this before._

_Four times._

_No. Absolutely not. No, no, no, **no**_ **.** _He was not about to watch Cas die again._

“When Jack was dying, I-”

“You made a deal to save him,” Dean interrupted, glancing behind him nervously at the innocent-looking wall. 

Castiel blinked in surprise and then again in confusion when Dean didn’t seem particularly angry at that fact. “The… the price was my life,” Castiel continued carefully, and Dean’s stomach contorted with an overwhelming feeling of _wrongness_. “When I experienced a moment of true happiness, the Empty would be summoned and it would take me, forever.” 

Dean narrowed his eyes at Cas. “Uh-huh. Hey, do me a favour, Cas? The speech you’re about to give me? Save it for when we get out of here, okay? Now, help me find a way out of here.” Whatever was sending him back in time had done so on three occasions now. Perhaps whatever it was wanted him to save Cas? 

Castiel looked a little shell-shocked. “I… I’m trying to give you a way. If you’d just hear me out-”

“No,” Dean growled, glancing over his shoulder again. “You’re about to sacrifice yourself to the Empty. Right after you drop a bomb on me that you… that you…” He shook his head and winced as Billie pounded on the door again. 

Castiel stared at him with round eyes. “Dean, we don’t have much time. Just listen-”

“No,” Dean snapped and Castiel jerked backwards at his viciousness. “No, I know what you’re gonna say. I’ve been through this _four times_ now. I am _not_ saying goodbye to you again.” He glanced around desperately for an escape route and clenched his fists when he realised that there wasn’t one because they were locked in a room with only one door and no windows. 

Castiel continued to stare at Dean with his mouth slightly agape. There was another ominous _bang_ from Billie and Dean raked a hand through his hair, panicking. 

“There has to be a way,” Dean muttered under his breath.

“…There is,” Castiel said quietly. “I always wondered, ever since I took that burden, that _curse_ , I wondered what it could be, what… what my true happiness could even look like. I never found an answer.” He managed a weak smile. “Because the one thing I want… it’s something I know I can’t have.” 

“Gonna stop you right there,” Dean growled, holding a hand up and watching as Castiel’s eyebrows furrowed in irritation. 

_That makes two of us._

“Dean, this is important and it would mean a lot to me if you could just-” 

“Cas,” Dean said exasperatedly as he marched towards the angel, “I love you, man, I really do, but we need to focus on getting out of here!” 

Castiel froze, staring at Dean with the expression of a deer caught in headlights. “I… you… what?”

Dean swallowed thickly and placed a hand on the angel’s shoulder. “You heard me. And look, we can talk about it all we want _when we get out of here_. Come on.” 

Castiel didn’t move, a tentative smile spreading across his face. “You… Really? You really mean that?”

Dean’s gaze softened and he cleared his throat awkwardly. He wasn’t really ready to out himself like that just yet, but he had no intention of watching Cas die again and if this was the only way that he could prevent the angel from sacrificing himself, then he would lay his pride and nervousness on the line and admit to the angel he loved that he… well, that he loved him. 

After all, it wasn’t as though he was worried about being rejected when Cas had confessed his own feelings three times already. 

He shrugged as nonchalantly as he could. “Course I do, Cas. And I promise that we’ll talk once we’re both safe.”

There was a wet _slurp_ and from the corner of his eye, Dean spotted the swirling pit of the Empty open up on the far wall. _Wait… Billie wasn’t in the room yet… Why had it appeared so early…?_

Dean was distracted by the joyous smile that exploded over Castiel’s face. “You love me?” he asked, as though he couldn’t quite believe it. 

Cas’ smile was infectious and Dean found himself reciprocating. He squeezed the angel’s shoulder in a subtle promise and was about to urge Cas to help him once more when suddenly, a dark, dripping limb shot towards Castiel and wrapped around his waist. 

Castiel’s eyes widened in horror and he snapped his gaze up to Dean.

 _Crap._

“Dean, I-” Castiel yelped before the Empty covered him completely and dragged him towards the wall.

Dean startled and sprinted after the captured angel, stretching for his shoulder only to miss by an inch as the Empty swallowed Castiel and abruptly vanished. 

Dean stared at the bare wall.

Billie chose that moment to kick down the door. 

With a terrible pain in his chest and a feeling of despair washing over him, Dean turned slowly to face Billie. She glanced around the room curiously, the rot on her arm creeping higher as she stalked inside, scythe clenched tightly between her fingers. When she noticed that Castiel was missing, she smiled darkly at Dean. 

“Time’s up,” she purred.

Head swimming from losing Cas earlier than expected, Dean eyed the door and made an ill-devised break for it. He ran exactly four steps before Billy swung the scythe towards his neck. 

There was a sharp pain around the point of his jugular and Dean’s vision abruptly plunged into darkness.

* * *

“Everybody’s gonna die, Cas, _everybody._ ” Dean stared at the floor as waves of helplessness swept over him, dragging him under, drowning him. “I can’t stop it.” 

Castiel looked no brighter. He turned to the door and a rune ignited upon its surface in fiery orange.

“She’s gonna get through that door,” Dean said miserably. 

“I know,” Castiel responded, equally as miserable.

“And she’s gonna kill you, and then she’s gonna kill me,” Dean continued wretchedly, before he paused and remembered having said that sentence five times now. Castiel spared him a brief, sorrowful glance and Dean’s whole body stiffened because he knew how this scene ended and so far, he’d been unable to change Castiel’s fate. 

“I’m sorry,” he whispered sincerely, because he’d failed Cas too many times now and he needed to come up with a win for them. Castiel turned away in defeat.

Then, Castiel’s expression changed and he slowly returned his gaze to Dean. “Wait, there is… there’s one thing she’s afraid of. There’s one thing strong enough to stop her.” 

Dean’s eyes widened. He was not letting Cas get eaten by the Empty again. How did he stop it, though? The Empty had appeared early last time and Dean didn’t understand why. What had he changed to make it take Cas and not Billie? What was it that Cas had told him four times already? Something about true happiness?

“When Jack was dying, I… I made a deal to save him.”

Dean nodded, listening carefully this time, because he needed to figure out how to stop the Empty from appearing. 

“The… the price was my life,” Castiel continued, watching Dean’s expression closely. “When I experienced a moment of true happiness, the Empty would be summoned and it would take me forever.” 

_That was it!_

He just had to stop Cas from feeling true happiness and then the Empty couldn’t take him! The question was: how did he do that? 

“I always wondered,” Castiel continued cautiously, as though concerned that Dean had yet to respond to him, “ever since I took that burden, that _curse_ , I wondered what it could be, what… what my true happiness could even look like. I never found an answer.” He managed a weak smile. “Because the one thing I want… it’s something I know I can’t have.” 

Dean’s stomach dropped. He suddenly realised what he had to do and he was going to hate himself for it.

“But I think I know… I think I know now,” Castiel said softly. “Happiness isn’t in the having. It’s in just being. It’s in just saying it.” 

Guilt flooded Dean’s veins and he dropped his gaze, uncertain if he could go through with his plan, knowing how it would make Cas feel.

“I know how you see yourself, Dean. You see yourself the same way our enemies see you,” Castiel said, determination filling his voice. “You’re destructive and you’re angry and you’re broken. You’re… you’re _‘Daddy’s Blunt Instrument’_. And you think that hate and anger, that’s… that’s what drives you. That’s who you are.” 

Castiel lifted his chin, eyes wide and pleading and filled with _so much_ desperation and anguish. _“It’s not,”_ he said fiercely. “And everyone who knows you sees it. Everything you have ever done, the good and the bad, you have done for love. You raised your little brother for love. You fought for this whole world for love. _That_ is who you are. You’re the most caring man on Earth. You are the most selfless, loving human being I will ever know.” 

There was a tightness in Dean’s chest. Could he really do this to the angel he loved?

“You know,” Castiel said with a bitter sort of smile, “ever since we met and ever since I pulled you out of Hell, knowing you has changed me. Because you cared, I cared. I cared about you. I cared about Sam. I cared about Jack. I cared about the whole world because of _you_. You changed me, Dean.” 

Dean swallowed and forced himself to say his own line. “Why does this sound like a goodbye?”

Castiel’s face crumpled even as his mouth curved into a sad smile. “Because it is.”

Something cracked inside Dean’s chest.

“I love you,” said Castiel.

Dean twisted his expression into one of disgust. “ _What?”_ he asked, voice dripping with revulsion as he heard the Empty open up behind him. He resolutely ignored it and narrowed his eyes at Castiel, watching the hope in his eyes flicker and fade to shock and hurt. Dean stomped down on his own feelings of self-loathing. “You’ve got to be kidding me? You choose _now_ to do this? As if I don’t have enough problems!” Dean hissed as he gestured to the door Billie was about to kick down in 3… 2… 1…

_Bang._

Castiel flinched – whether it was because of Billie or Dean’s words, Dean wasn’t certain – and stared at Dean brokenly. 

“Dean, I-”

“No,” Dean growled. “You’ve said enough. You were right to keep it a secret. And if that’s the one thing you want, then you definitely can’t have it.” 

Behind them, the Empty hesitated and Cas’ expression crumpled. Billie prowled closer, scythe at the ready.

“We’ll talk about this later,” Dean snarled, burying his own self-hatred as he hacked at his angel’s heart. “If there even is a later. I can’t believe you wasted all that time to tell me _that_. You’ve always been selfish.” 

Definitely not true, but if it kept the Empty at bay, Dean wouldn’t take it back.

Anger flicked briefly across Castiel’s face before he shook his head with a bitter smile. “I suppose I have nothing to lose, then. You may think it disgusting, but I can’t change my own feelings. I’ve confessed to you and I’m at peace with my decision. Knowing your answer is almost a relief, expected even.” Castiel turned to the Empty and it seemed to grow excited, sloshing and undulating faster, as though waiting for permission. 

Dean blinked. _Expected?_ Wait, had Cas always believed that Dean would be repulsed by his feelings?

“This is still my moment of true happiness,” Cas said softly. “Knowing he doesn’t feel the same way is of no consequence. I’ve admitted my own burden and I… I feel that’s enough. I’m happy that he knows.” 

A limb raced out of the Empty, grabbing Billie first before a second headed towards Castiel.

Heart racing wildly, Dean moved on instinct, dodging Castiel’s hand before he could once again hurl him into the wall. He tackled the angel out of the way and the Empty sailed past them. Castiel stared at him in surprise and Dean shot him an apologetic look before grabbing Cas’ arm. The dripping, black limb reared in anger and hurtled towards them again, and Dean sprinted towards the open door, dragging Castiel with him. 

The Empty chased after them, down the bunker’s corridors, and Castiel looked terribly confused as he stumbled after Dean. 

“It won’t stop!” Castiel yelled as the terrifying limb crashed into a wall and broke several lights before morphing into a water-like form and beginning to flood the hall. “Dean, let me go!” 

“No!” Dean snapped as he tightened his grip on Cas’ arm and pushed himself faster. “I’m not watching you die again! I’m not going through this a fifth time!” 

“What are you talking about?” Cas asked exasperatedly as the lights began to flicker and buzz before going out completely. Dean led them down another corridor and the Empty slithered after them. 

“This isn’t the first time we’ve done this,” Dean panted. The War Room was so close. Just a little further and they would be out of the bunker. “I had to think of something.” He didn’t dare look back in fear of tripping. “I’m sorry.” 

“Wait… what?” Castiel asked and Dean could hear the budding hope in his tone. Dean held him tighter. He loved that Castiel believed him without hesitation – that he didn’t scoff or fire accusations at Dean despite everything he had said in that room. 

The Empty was gaining ground.

“I love you,” Dean said, legs beginning to ache as they raced through the War Room. “Of course I love you. But can we talk about this later? When we’re not being chased?” 

Castiel fell quiet and Dean _really_ hoped that he wasn’t going to sacrifice himself again, like the angel was prone to doing.

“I need you,” Dean added desperately, just to make sure that Castiel understood. “I can’t do this alone again.” 

Castiel didn’t respond, but he didn’t pull away either, so Dean kept running. They took the stairs three at a time and Dean released Castiel’s arm to throw the front door open. 

“Dean!” Castiel screamed suddenly and Dean turned to watch the black sludge climb over Castiel’s shoulders and begin to envelop him. 

Dean’s stomach bottomed out and his first instinct was to grip Cas’ arm again and tug. When that didn’t work, he threw himself at Castiel and wrapped his arms around him, holding him close as the Empty swallowed them both. 

Distantly, Dean heard Cas shout _“No!”_ and he wound his arms tighter around the angel, even when Castiel tried to push him away. 

Dean’s world went dark.

* * *

When Dean next opened his eyes, he was staring into bright pools of blue. _Distressed_ pools of blue. _Angry_ pools of blue. 

Castiel shoved at his chest and Dean let himself stumble backwards without falling too far away from Cas.

He looked around cautiously and saw nothing but black. A shade of black that Dean hadn’t even realised existed. There were no walls or floors, just never-ending darkness and Dean didn’t know if he was standing on it or being suspended within it. 

“Why did you do that?” Castiel seethed, clenching his fists. “Why didn’t you just run? You should have left me!”

Dean scowled and sidled closer. “I was desperate. I wasn’t about to let you go without a fight.” 

Castiel threw his arms up and gestured to the endless nothing around them. “And now we’re both stuck here.”

“Did you _want_ me to let you die?” Dean snapped. “Did you _want_ to just give up?” 

“I made a _deal_ ,” Castiel hissed. “I understood the consequences. I was trying to save _you_.”

Dean stalked towards Castiel and grabbed his coat. “Do you know how many times I’ve watched you die for me? Do you know how many times I broke at seeing you sacrifice yourself? I’m not going through that again. I’m not letting you go through that alone again. At least if we’re together, we can figure something out. We’re family, remember? We don’t give up on each other.” 

Castiel gazed at Dean’s white-knuckled grip on his lapel and finally, his shoulders sagged. “Okay, Dean. We’ll figure something out.” 

With a burst of courage, Dean leaned in to press his lips sweetly to Cas’. A second later, he pulled away and smiled softly at Cas’ shocked expression. 

“We’ve a lot to look forward to,” Dean promised quietly and Castiel’s eyes brightened with excitement. Dean released the angel and looked around them. “First, we’ve got to work out how to leave this place.” 

“Let me help you,” said a familiar voice and Dean and Cas whirled around to face a figure from their past, glaring angrily at them.

“…Meg?” Dean asked in surprise.

“Not quite.” 

“The Shadow,” Castiel whispered to Dean. “Caretaker of the Empty.”

Dean frowned and the Shadow edged closer. It stretched a finger towards Dean. “You’re not supposed to be here.” 

Dean threaded his fingers with Cas’. “Neither is he.”

The Shadow smiled in a pained manner. “Yes, he is. We made a deal.” It narrowed its eyes at Castiel. “You said nothing about a plus one.” 

“Thought I might get lonely,” Cas said tightly.

The Shadow shook its head. “No plus ones. No humans. You sleep and then, I can sleep. There’s nothing else.” 

“Bet you’re fun at parties,” Dean said drily before plastering on a smile when the creature turned to glower at him. “Look, we can get out of your hair and then you can get back to sleeping, how does that sound? If you could just open a door for us…” 

The Shadow grinned toothily. “You don’t get to make demands, human. Not here. Not to me. Say goodnight to your angel friend.” 

Dean turned to Cas with wide eyes and watched as the angel crumpled to the floor in a heap, seemingly passed out. He made to round on the Shadow, only for the nothingness below his feet to suddenly become something. 

A _hole_ , to be precise.

He screamed as he fell, but he didn’t fall for all that long because he opened his eyes and found himself standing at the top of the bunker’s stairs, exactly where he and Cas had been absorbed by the black ooze. 

He looked around frantically. “Cas? Cas!”

 _Not again._ _Please, not again. They were so close!_

Dean sunk to his knees, grasping the rail for support. He had failed, again.

* * *

Dean didn’t let Chuck live this time. He was sick of being pummelled by the guy – it was his fifth time in this hellish loop after all – and he didn’t see what difference it would make if he just knifed Chuck the moment he became human. 

Sam was shocked and Dean wasn’t all that sure why. He couldn’t particularly remember why they hadn’t killed him the first time. 

Jack disappeared, as usual, and Dean took up drinking again. He didn’t stop hunting and he grew more reckless, uncaring if he got wounded or concussed or _shot_. Sam tried to get him to talk, but Dean didn’t see the point since he would probably be thrown back in time again anyway. He eventually figured out that the pie at the festival was cursed or hexed and when he sat on the bench beside Sam, he didn’t even ask his brother what was wrong before he took a bite of the pie out of morbid curiosity. 

It was as he felt his heart race and his vision fade that he realised that there was no magic spell cast upon the pie, just plain old poison. 

He died, for the fifth time.

* * *

Dean watched silently as Castiel ignited the rune magic upon the door Billie would ultimately burst through. He said nothing as Castiel dropped his gaze defeatedly, both of them knowing that there was no way out. 

“Wait, there is… there’s one thing she’s afraid of. There’s one thing strong enough to stop her.”

Dean raised his eyes to meet Castiel’s in a sad gaze.

“When Jack was dying, I… I made a deal to save him.” _Because that’s what Cas did. That’s what Cas always did; save the people he loved, even if it meant dooming himself_

“The… the price was my life,” Castiel continued as Dean edged nearer, heart breaking for the angel in front of him. Why could Castiel never have what he wanted? What he deserved? “When I experienced a moment of true happiness, the Empty would be summoned and it would take me, forever.” 

Dean stood mere inches away from Castiel and the angel gazed up at him with a bittersweet smile.

“I always wondered, ever since I took that burden, that _curse_ , I wondered what it could be, what… what my true happiness could even look like. I never found an answer.” He managed a weak smile. “Because the one thing I want… it’s something I know I can’t have.” 

Dean huffed a humourless laugh before cupping Castiel’s cheek and pressing their mouths together gently. Castiel made a startled sound and Dean pulled away. 

“You could have if you’d just asked,” he whispered as the Empty yawned wide behind him.

Castiel gazed up at him with joy and love and confusion burning behind his eyes, and then his face crumpled as he realised what was about to happen. 

Dean slid his arms around Castiel’s waist, blocking the angel’s view of the Empty. He ignored Billie’s attempts to break the door down and he smiled at Cas. 

“You are the best thing that ever happened to me,” he murmured as Cas’ eyes glistened with grief. “You mean so much to me and I didn’t tell you enough. Didn’t thank you enough for always being there. You always helped me, even when I didn’t deserve it, even when I treated you like crap. You’re the best friend I could have ever asked for and I wish we could have been more. I wish we could have had more time.” 

Castiel gripped Dean’s arms, a weak smile curving his lips. “Thank you,” he whispered.

Dean stroked his thumb down Cas’ cheek. “I love you, too.” 

Castiel shook his head, tears glazing his eyes. “I didn’t say it, yet.” He was still smiling.

Dean allowed himself a soft chuckle as he leaned their heads together. “You were going to.” 

The Empty slurped and sloshed eagerly, and Dean shielded Cas from it, ensuring the angel couldn’t see his horrific fate.

Castiel squeezed Dean gratefully before placing a hand on his shoulder, and Dean knew that there would be a handprint on his jacket once Cas lifted his palm. “Goodbye, Dean.” 

“Don’t,” Dean pleaded quietly and Castiel paused. “Don’t push me away. Let me hold you?”

Castiel frowned in confusion but eventually nodded and allowed the hunter to press his face into his neck. He stroked Dean’s back gently and Dean choked back a sob when Cas dissolved beneath his fingers. 

He straightened, not bothering to wipe away his tears as Billie barely made it into the room before the Empty grabbed her too. 

He sighed and left the room. In fact, he left the bunker entirely and slid into his car. He should have driven to Sam and Jack – that’s what he was supposed to do. He didn’t. What was the point? He would live through another month before being thrown back to the same point and he would have to watch Cas die again. An endless loop of losing Cas, then Jack, before dying himself. Hell was preferable to this. 

Instead, he drove towards the nearest lake and locked the doors. He allowed the lake to swallow his beloved Impala and when he felt water lap at his shoes, he leaned back into his seat, closed his eyes, and smiled peacefully.

* * *

The next time he found himself in that room with Castiel, Dean had managed to scrape up a meagre slither of hope. He couldn’t allow his thoughts to spiral like they had last time; he owed it to Cas and Sam and Jack to find a way out of this mess, to find a way to save all of them. 

He was Dean freakin’ Winchester and he _would_ save his family _and_ the rest of the world. Just like he always did.

“Wait, there is… there’s one thing she’s afraid of. There’s one thing strong enough to stop her,” Castiel said, predictably and Dean came up with a plan. That was the problem, wasn’t it? They were being too predictable! They needed to catch Billie off-guard, to do something utterly insane and idiotic and maybe, _just maybe_ , they might get the chance to escape. 

Sure, they couldn’t hide from her forever, but if they could keep the Empty at bay and keep running until Jack received Chuck’s powers… He would put Billie back in her place and they could deal with Cas’ arrangement with the Empty once they were out of Death’s grasp. 

“Dean? What are you- Dean!”

Dean grinned at Castiel as he threw the door open and watched Billie pause in surprise. He didn’t give her time to think before he grabbed her scythe and swung it at her middle in the same way he had killed the original Horseman. Her eyes widened and she leapt backwards, so Dean swung again, mildly dismayed when she caught the weapon with one rotting hand and glowered at him. 

“Bad decision,” she growled at him before yanking the scythe out of his grip and twirling it effortlessly like it was made of paper. 

There was a sharp pain in Dean’s side and he glanced down to find himself impaled between two ribs.

 _Whoops._

“Crap,” grumbled Dean as his own blood trickled down the polished metal blade. Billie dragged the scythe out of him painfully and he slumped to the floor, slamming a hand over the wound to stop his insides from slipping out. Behind him, Cas screamed his name in horror. 

Dean swallowed thickly as he felt consciousness slipping from him. He smiled up at Billie thinly.

“See you in a few minutes.” 

She frowned, puzzled and Dean couldn’t keep his eyes open long enough to see Cas lunge for Billie. It was probably for the best, because Cas didn't win the fight.

* * *

Dean eyed the discarded book in the corner of the room. It was a stupid idea, absolutely deplorable… but Dean was running out of options and if it would save Cas from the Empty… 

He had to at least try.

He made his way over to the book and Castiel watched him miserably. 

“Wait, there is… there’s one thing she’s afraid of. There’s one thing strong enough to stop her.”

Dean ignored him and plucked the book from the floor, inspecting its weight by turning it over in his hands. He meandered over to Cas as the angel continued, “When Jack was dying, I… I made a deal to save him.” 

Dean nodded and let the heavy book drop to his side as he came to stand in front of Cas. The angel gazed at him solemnly. “The… the price was my life.” 

Dean smiled, raised the book and in one smooth movement, slammed the cover into the side of Castiel’s head.

The angel dropped like a stone, unconscious and Dean grimaced apologetically. He tossed the book to the floor and flicked his gaze to the door, waiting patiently. 

He didn’t have to wait long before Billie burst into the room. She stared at Castiel’s limp form and raised an eyebrow at Dean. 

He shrugged at her. “I’m trying something new,” he said truthfully, relishing her disturbed expression.

She brandished her scythe and Dean realised that he had nothing to defend himself with. He eyed Castiel’s angel blade, clasped between the angel’s fingers, but decided that it would do no good since Billie was immune to it. He cocked an eyebrow at the book and picked it up once more. 

Billie scoffed and advanced on him, scythe aimed directly at him.

Dean waited for Billie to be within a few feet of taking a swipe at him before hurling the book at her head. It made a dull _thud_ as it connected with her face and she grunted, jerking backwards slightly. The movement gave Dean enough time to sprint forwards and grab the scythe from her lax hold. 

He twirled it almost expertly and rammed the blade through her neck, and she barely had time to process his attack before her head detached from her body and she crumbled to dust. 

He watched the scythe dissolve and he blinked a few times before his eyes widened in shock and he whirled around to find Castiel still sprawled over the floor. He threw his hands up, fist pumping the air in excitement as a grin crawled over his face. 

_He did it!_

He trotted towards the angel, eying the bare wall where the Empty had yet to appear, and he grinned wider as he picked Castiel up. 

Cas stirred as Dean supported him and an adorable frown creased his brows. Dean clamped his mouth shut and dragged Cas towards the door. 

They weren’t out of the woods yet. If Cas managed to admit his love for Dean or Dean gave any inclination that he might reciprocate the angel’s feelings, the Empty would swoop in and steal him away again. He couldn’t let Cas know yet – had to stop the angel from confessing to him at all costs, just until they beat Chuck and Jack could mollify the Empty. 

Castiel blinked sluggishly. He glanced over at Dean, opened his mouth and closed it again as if he wasn’t quite sure what had just happened. 

“Dean?” Cas asked weakly as they made it into the corridor and Castiel remembered that his legs worked. He attempted to walk by himself only to stumble, so Dean caught him and came to a halt, allowing the angel to regain his balance. “I don’t… Where’s Billie?” 

Dean grinned. “Dead.”

Castiel blinked slowly, processing the statement. “How?” 

“I killed her,” Dean replied, staring into bright blue eyes and privately thinking how expressive they were. Enticing. Perhaps that was why he stared into them so often – often enough for Sam to tease him, anyway. 

Irritation filtered into that gorgeous gaze and Dean braced himself.

“You… you hit me,” Castiel pronounced slowly, testing the words out. “With a book.” He scowled. “It hurt. Why would you do that?” 

Dean hesitated. He couldn’t tell Cas that he had done it to prevent him from summoning the Empty and he couldn’t tell him that it was to save his life. _Should he lie?_

He swallowed. “I… You’re just gonna have to trust me, Cas,” he offered gently. “I promise I’ll tell you when I can, but right now… it’s not an option. Wait and I _promise_ I’ll explain everything.” 

Castiel looked ready to object, but then he paused and nodded. “…Okay. I trust you.”

 _Of course he does. He always has._

Taking a deep breath, Dean stamped down on the urge to kiss Cas. He just had to wait until they beat Chuck and then this wonderful angel was his. Castiel had hidden his feelings for far too long now and Dean was determined to make it up to him. 

“Come on,” Dean murmured. “We have a world to save.”

Castiel smiled warmly and allowed Dean to lead him out of the bunker.

* * *

Dean felt more hopeful than he had in _weeks_. Or at least more hopeful than the last seven times he had lived through it. 

_Cas was alive_.

 _And_ he had somehow convinced Michael to remain on their side. It had been surprising since Dean had never thought to talk to Michael or Lucifer amidst his worsening throes of depression, yet Castiel had obviously figured out Michael’s plans far quicker than he and Sam had and he took the archangel to the side and conversed lowly with him. A few hours later, Dean saw the change in Michael’s eyes – the determination that had replaced his previous hopelessness. 

Cas was awesome like that.

They appeared before Chuck as a small army and at first, Chuck laughed and turned to Michael expectantly. Michael narrowed his eyes and summoned his weapon. 

The smile was quickly wiped from Chuck’s face, to be replaced by anger.

“Ungrateful brat,” growled Chuck as he raised his hand to snap his fingers. 

Dean had the advantage that he had been through this several times and he knew Chuck’s next move. He could have allowed Chuck to destroy Michael, but he was curious and tired of being beaten to a bloody pulp and so, he whipped out his gun and fired into Chuck’s hand. 

The small man cried out – from shock or pain, Dean wasn’t certain – and he swivelled to face Dean.

“You’re not destroying him this time,” Dean said, half wondering if Chuck would understand the implications that they had done all of this before. It had certainly crossed his mind that Chuck was behind all the ‘resets’. 

However, Chuck screwed up his face in confusion before gritting his teeth.

“You know, eternal suffering sounds good on paper, but as a viewing experience, it’s just kind of… meh. So,” Chuck said with a tight smile, “we’re done. I’m cancelling your show.” 

Sam shook his head angrily. “Alright. Well… one for the road.” He clenched his fist and rammed it hard into Chuck’s mouth, only to recoil with a wince and a pain in his knuckles as though he had just punched a particularly solid rock. 

Chuck’s smile grew amused. “Cute.” He threw his hands out and Sam and Dean doubled over with identical groans, clutching at their stomachs as agony swept over their expressions. 

Michael and Castiel shared an alarmed glance as Chuck raised his hand to click. They surged forwards together; two warriors uniting to defeat a shared enemy, and before Michael had a chance to brandish his archangel blade, Chuck whirled on his heel and flicked a hand in their direction. Both angels were thrown down the beach, giving Sam and Dean a chance to rise to their feet and take a swing at Chuck. He caught their fists easily and two gruesome _cracks_ penetrated the air as Sam and Dean wailed in blinding pain. They clutched their broken arms and Chuck laughed sinisterly. 

“What the heck. I can get my hands dirty.”

He slammed his knuckles into Sam’s jaw first and then Dean’s and both Winchesters tumbled to the ground at the inhuman force. When they opened their eyes, Michael was behind Chuck, eyes burning a furious blue and blade at the ready. He skewered Chuck in the back and Chuck snarled as he raised a hand to destroy his son. 

Suddenly, Castiel was in front of Chuck – having sprinted across the beach – and he caught Chuck’s hand before forcing his blade into his palm. Chuck cried out and Michael quickly wrapped his arms around the smaller man, holding him in place as he slid his blade out of his back and tossed it to Castiel. 

Castiel gestured Jack over hurriedly and Chuck fought against Michael’s grip as Castiel sliced the blade through his throat. 

Impossibly white light bled from the wound and Jack muttered a few words under his breath and parted his lips, allowing the light to snake between them. Chuck nearly broke out of Michael’s grip, but Castiel grabbed his wrists as Sam and Dean scrambled to their feet and rushed over to help. 

Chuck’s struggling grew weaker as Jack’s eyes brightened and soon, Chuck slumped in Michael’s grip, exhausted. Michael released him with a disdainful glance and he crumpled to the floor with a whimper. 

As though proving a point, Michael joined Castiel and the Winchesters’ sides and Jack stepped back, staring down at his grandfather in pity. 

Chuck looked up at them with a bitter smile. “You know, for the first time, I have no idea what happens next.” He pulled the blade from his palm and winced as blood seeped from the wound. “Is this where you kill me?” 

Dean had no desire to listen to the same speech again and he interrupted the man before he could continue.

“Nah, see, this is the ending where you die like all the other humans you forgot about. The ending where you grow old, you get sick, and you just die. And no one cares. And no one remembers you.” Dean smiled cheerfully. 

Chuck stared for a long moment before blinking when the group began to leave.

“Guys. Wait. No. G-guys!” He scowled at their retreating backs. “You… It wasn’t supposed to be like this! Michael! You were supposed to come back to me! The perfect soldier! You were mine!” 

Michael turned a cold gaze upon him. “You left me to rot in the cage. And you know what? You left Lucifer too.” Pain crept behind his eyes, mixed with regret. “You left both of us to fight and you pitted us against one another to fit your _story_. And then, you took Adam. Well, guess what? I’m writing my own story from now on. Goodbye, _Chuck.”_

Chuck stared at him with wide eyes as he held his head a little higher and followed the Winchesters.

Chuck scrambled to his feet. “You weren’t even supposed to be here, Castiel! You were supposed to be dead!” 

Castiel frowned in brief confusion before shaking his head and ignoring the desperate human.

“I wrote it!” Chuck insisted. “I wrote that you died at the hands of the Empty!” 

Dean’s eyes widened in alarm and he tried to hurry the group into the car.

“This isn’t right! You should have admitted your forbidden feelings for your favourite Winchester and the Empty should have come for you!” 

Castiel’s eyes blew wide and round and Dean shoved the angel into the car and slammed the door, heart racing as Michael, Sam, and Jack stared holes into the side of his head. 

Dean threw the car into gear and sped away, palms growing sweatier the longer the silence stretched on.

“…Dean-” 

“We’ll talk later,” Dean said, chest beginning to heave. They weren’t in the clear yet but he could tell by Castiel’s deer-in-headlights expression that the angel wanted to talk _now_. “Cas, please, I promise we’ll talk later.” 

Castiel shook his head slowly. “No, he… he’s right. I’ve been keeping it to myself long enough. I have something to confess-” 

“A lot of other dudes in the car. If you could just wait a little longer-” Dean couldn’t breathe. _Not now! Not after all this work to get here!_

“Let him talk,” frowned Sam before he turned a patient gaze to Castiel. “What is it you want to say, Cas?”

“Don’t!” Dean yelped as Castiel opened his mouth. “Cas, I’m begging you! Whatever you’re about to say, _don’t_.” 

Castiel gestured vaguely to the window. “Chuck has practically said it for me!”

“Great!” Dean snapped. “Then we don’t need to discuss it.” 

Suddenly, Castiel blinked and stared at Dean in astonishment. “Wait… you… already know, don’t you?” He looked terribly confused. “You somehow worked it out and now you… you don’t want me to say it. Do you… Are you disgusted?” He looked heartbroken and Dean hated himself for it, but he couldn’t let all this work go to waste! 

“Not disgusted. Just uncomfortable,” Dean lied.

Castiel sagged at the rejection as Michael squinted at Dean. 

“He’s lying,” Michael announced abruptly. “He doesn’t feel that way at all.” He was confused as to what they were actually discussing, but he seemed confident that Dean wasn’t being truthful about it. 

Castiel raised his gaze, a frown pinching his brow.

“What? No, I’m not,” Dean said quickly, far too quickly. 

“You’re not lying about how you feel, or you’re not disgusted?” Sam asked.

“I’m not disgusted,” Dean scowled before his eyes widened and he shook his head. “No, I mean I’m not lying about loving Cas.” 

Cas’ eyes blew wide and a grin crawled over Sam’s face. “Wait, so you do love Cas?”

“Yes,” Dean said exasperatedly before stiffening and shaking his head. “Wait, no! I didn’t mean that!” 

“You’re in love with Cas?” Jack asked, sounding extraordinarily pleased.

“I’m… not _not_ in love with Cas,” Dean said, confusing himself further. He thought about the sentence and shook his head again. “Wait, no, that’s not right. Look, can we talk about this later?” 

Castiel’s gaze softened and a smile touched his lips. “Of course, Dean.”

There was a wet _pop_ and Dean glanced through his mirror at Cas. “No!” he snapped. “No, wipe that smile off your face! It’s not…” From the corner of his eye, he caught sight of the black tendril. “I don’t love you!” he said desperately. “It’s not like that!” 

“Dean-”

“ _Shut up, Sam!”_

The car shuddered and rattled and Dean slammed his foot on the gas.

“Are cars supposed to do that?” Michael asked gingerly as Castiel glanced through the window and went pale as he, too, spotted the black ooze chasing them. 

“Oh,” he whispered as he looked at Dean, grief-stricken. “Do you know about…?”

“The deal?” Dean snarled. “Yes! I know about your idiotic deal!” 

Jack glanced through the window and straightened. “Wait, maybe I can talk to it? Break the deal?”

“What deal?” Sam asked, befuddled. “Wait, what’s happening?” He glanced through the wingmirror and stiffened at the wretched darkness following them. “What is _that?!_ ” 

Dean growled to himself and suddenly yanked on the wheel, throwing the car around a sharp corner. The Empty easily slithered after them. 

Dean cursed, sweat collecting at the nape of his neck. _This couldn’t be happening. Not now. Not after they’d come all this way!_

“I lied,” Dean blurted desperately, clutching at straws. “I didn’t want to upset you.” He caught Cas’ gaze through the mirror. “I really don’t feel that way about you. You’re my brother and that’s it. That’s why I wanted to talk to you about it later – when we were alone. I didn’t want to… ah… embarrass you.” 

Castiel smiled sadly at Dean and shook his head. “It’s alright, Dean. I know what you’re trying to do. It won’t work. It isn’t about me saying the words – it’s about how I _feel_. The Empty was never interested in my words, only how I feel when I’m around you. How _you_ make me feel.” 

Dean swallowed thickly, breaths coming faster. He eyed Jack through the mirror. “Please,” he begged quietly. “Please save him.” 

Jack nodded, determination filling his gaze and suddenly he vanished from the back seat, leaving a gaping space between Michael and Castiel. Castiel gazed at Dean for a moment before he frowned in realisation. 

“…That’s why you knocked me unconscious, isn’t it? You didn’t want me to confess.”

Dean remained quiet, watching as the black tendrils behind them slowed and paused in the middle of the empty street, listening, contemplating. Dean didn’t allow the car to slow and he kept driving until he could no longer see the repulsive blackness. 

“You… you were trying to save me,” Castiel continued softly before tilting his head in that familiar bird-like manner. “But I don’t understand… How did you know that I was going to admit anything to you? And how did you find out about the deal? Did Jack tell you?” 

Dean carefully pulled over, nervously eying the back window for any stray tendrils. He allowed the engine to idle as he composed himself and then, he turned to Castiel with a neutral gaze. 

“This isn’t the first time I’ve been through this. Or even the second. I keep living the same nightmare over and over and when I die, I get thrown back to the same point in time – when we’ve got our backs to the wall and Billie is about to break in and the Empty has its jaws open for you. It’s always the same and I didn’t understand at first, but I think… I think whatever keeps throwing me back, it wants me to save you.” Dean swallowed and ignored Sam and Michael’s wide-eyed stares, focus entirely on Castiel. “This is the first time we’ve got this far. I can’t lose you again… I can’t go through another round of this. Promise me you won’t go down without a fight. Promise me you won’t just… serve yourself up to the Empty again.” 

Castiel blinked and nodded slowly. “I… I promise.” He squinted and took in the exhaustion behind Dean’s eyes. “How many times have you been through this, Dean? How many times have you… died and been hurled back through time?” 

Dean laughed hollowly. “Too many. I don’t know. Lost count.”

Michael’s brows pinched together. “Humans shouldn’t time travel. Their bodies are too fragile to withstand the fluctuating gravity of the time-space vortex. Repeated travel could tear their atoms apart. Or possibly compress them to the point of implosion. Depends on whether it’s a Tuesday or not.” He frowned thoughtfully. “Actually, perhaps Tuesday is the _only_ safe day for humans to time travel. I think Gabriel might have interfered with the time continuum at some point.” 

Sam balked, clearly desperate to ask questions, but Dean was developing a rather large headache and he rubbed at the bridge of his nose tiredly. “Whatever. All I know is I’m sick of watching Cas die and Jack become part of the _raindrops_ and I’m really beginning to hate pie.” 

Both Sam and Castiel glanced at each other in horror at that.

Dean waved a hand dismissively. “It keeps killing me. Look, it’s not important. I just… I really want this time to end happy for us, okay? Cas is alive, Michael’s on our side, Chuck’s powerless, and Jack is… well, I’m not sure what Jack’s going to do yet. Maybe he’ll stay with us, maybe he won’t, but things are… things are looking up right now. If we could just beat the Empty-” 

“Hi.”

They startled at the sudden appearance of Jack. He smiled at them and Dean immediately glanced through the back window, scanning for the Empty. 

“It’s gone,” Jack assured with a grin. “I made a deal.”

The adults turned to him in horror and Jack shook his head in amusement. 

“Not that sort of deal. I took all the demons and angels out of it and stuffed them back into heaven and hell. They’re a little confused at the moment and recovering from being woken up, but the Empty can finally go back to sleep without interruption. That’s all it wanted. I’ve also rerouted the angel-demon death system so that when one of them dies, they go to either heaven or hell, just as humans do. I made a couple of loopholes though, so that if a demon becomes Good, it can go to heaven and if an angel strays from Good, it can go to hell. Like the carrot and stick metaphor that Sam taught me.” He smiled at Sam and Sam huffed an impressed laugh. 

Dean checked his watch. “It’s been… six minutes.”

“On Earth,” Jack pointed out. 

Dean nodded slowly, content not to argue. “So… Cas is…?”

“Safe,” agreed Jack. “No more resets.” 

Dean let out a hysterical laugh before gathering himself. “And… and you?”

Jack tilted his head thoughtfully. _He was so like Castiel._

“I… need to fix the other worlds. And this world. And demons and angels need guidance.” He watched Dean’s face fall and he smiled reassuringly. “But… I’ll be around! And you can always… ah… pray to me. Or call me!” He frowned. “I should probably give heaven cell signal.” 

Dean allowed a small smile to curve his lips. “You’ll check in though, right? I get you want to be a ‘hands-off’ all-powerful being, but, um… you’re still family. It’d be nice to see you once in a while.” 

Jack’s eyes crinkled in amusement. “I haven’t said anything about being ‘hands-off’ yet. You really have been through this multiple times, haven’t you?” 

Dean dropped his gaze, unwilling to discuss it. Too many deaths. Too much trauma and heartache.

Jack seemed to soften. “I’ll drop in. This is a lot for me to manage.” He grinned cheekily. “And I am only three years old. Might have the knowledge of _everything_ , but I’m not quite street smart, right, Dean?” 

Dean perked up, daring to hope and Jack continued, eyes glinting with mischief. “I’ll definitely need my parents’ advice every now and then.” 

Dean laughed joyfully for the first time in too long. Castiel gazed down at Jack adoringly and Sam grinned proudly. Michael gazed out of the window out of politeness until Jack gently touched his shoulder. “Perhaps my uncle could also give me a few tips? After all, you’ve been running heaven for a long while now.” 

Michael looked ashamed. “I did an awful job at it.”

Jack tilted his head and suddenly, Michael’s eyes widened and he seemed to gaze at nothing for a few moments until Jack caught his attention. 

“You were hurt from being abandoned and overwhelmed when everyone looked to you for leadership. This time you’ll have your favourite human to keep you grounded.” 

Jack smiled patiently as Michael whispered, “Adam?”

There was a lengthy pause and Michael looked far away before a grin lit his face and he smiled at Jack gratefully. 

Finally, Dean felt a slither of happiness worm its way into his battered heart and he rolled the car onto the road.

“Alright, kid,” he said, “you ready to do your thing?” 

Jack raised his hand and clicked.

* * *

They drove past the pie festival and Sam and Castiel glanced at Dean in surprise. 

“You feeling okay?” Sam asked with a half-concerned smile.

Dean grinned, warm and exuberant. “More than okay!” He flicked a subtle glance to Castiel in the back seat and indulged himself in the memory of waking up in the angel's arms that morning. 

“Really? Because you didn’t even _look_ at that festival. Shouldn’t we be parked up and queuing for enough pie to make you physically ill?” 

Dean waggled a finger in the negative. “Nope! I’m thinking burgers. Or barbeque. Or, well, anything that isn’t a poisoned slice of pie!” 

He turned up the radio and bobbed along to Led Zeppelin’s _Ramble On_.

Sam and Cas shared a glance of realisation before falling quiet. 

Dean smiled and drove on.

* * *

Dean idly thought that the barn was familiar as he fought with the vampire mimes. Something about the smell of blood and fear and sweat and the rusting rebar jutting out of one of the support beams. It was odd since he had never visited it in any of his ‘resets’, yet the place oozed familiarity. 

Still, Castiel was alive, Michael was on their side, Jack was fixing… _everything_ , and Dean had vowed to make this his last hunt before he retired. Things were going swimmingly and he had a life to look forward to. 

He watched Castiel’s eyes light an intense blue as he burned up two vampires and headed for a third. Sam decapitated another and Dean followed suit with the vampire currently trying to rip out his throat with her teeth. She was familiar in a way the barn wasn’t – he could grasp the memory of her easily and he vaguely knew her name to be _Jenny._ Not that he particularly cared, but it was good to see that his memory wasn’t deteriorating in his old age. 

He sliced her head clean off and turned to the largest vampire in the room as Sam culled another.

Once this was over, he, Sam, and Cas had planned a movie night, complete with takeout and sugary treats. He was very much looking forward to curling up on the sofa next to his angel. Perhaps tomorrow, he could fill in a job application; get that apple pie life he’d always secretly dreamed of. Except he’d have a supernatural boyfriend instead of a wife. 

That suited him better anyway.

Castiel burned out another vampire and turned to the one Dean was targeting. He glanced at Dean and they shared a small smile before surging forwards as one. 

They killed him in less than three seconds and Dean looked around the barn curiously, impressed at how quickly they’d managed to fell the vampires. He still couldn’t shake the feeling of familiarity, but he could ignore it. 

“That was fun,” Dean hummed as he meandered over to the rusted rebar that looked oh-so-familiar. He ran a finger along it idly and chuckled as he turned to Cas. “Man, this could have been a hazard. Could you imagine if one of us got impaled on this thing?” 

Castiel tilted his head. “I’d rather not imagine that.”

Dean flicked the rebar and it rang dully. He watched Sam leave the barn, in search of the two children that had escaped. He sauntered over to Castiel and, whilst no one was around, slid his arms around his angel’s waist. 

“Hey,” he grinned as Castiel stumbled into him. The angel cocked an amused eyebrow at him. “Come here often?”

Castiel practically melted into his hold. “No, but I should inform you that I’m already taken,” he sighed, looking quite pleased with himself. 

Dean made a disappointed sound before tugging the angel a little closer. Castiel moved willingly. “I’m sure your boyfriend won’t mind,” purred Dean. “Come on, angel, let me show you a good time.” 

A smile quirked Castiel’s lips as he settled into the game. “I’m afraid I can’t let you do that, _human_ ,” he teased, hands snaking around Dean’s back. “You see, I’m very much in love with my boyfriend and I refuse to be disloyal to him.” 

Dean leaned in close and brushed his lips across Cas’ cheek. “Then he’s a very lucky man.”

Castiel closed his eyes and held Dean a little tighter. “Actually, I believe that I’m the lucky one.” 

**_“DEAN!”_ **

They startled at Sam’s shout and turned to the open door at the back of the barn. When there were no further sounds, Dean and Castiel shared a horrified glance before bolting towards the exit and scanning the area for Sam. The first thing they noticed was the creepy laughter of children. The second thing they noticed was that Sam was on the floor, said children hovering over him with identical grins. 

There was an _axe_ in Sam’s chest.

 _“SAM!”_ Dean howled as he sprinted towards his fallen brother. The two children bared their vampirish teeth at him before giggling and speeding off deeper into the forest. 

Dean skidded to a halt beside his brother and dropped to his knees, Castiel not too far behind.

“Sam?” Dean begged when his little brother didn’t open his eyes. “Sam!” 

There was no response and Sam’s head lolled to one side when Dean cradled it.

Tears pooled in Dean’s eyes. _No. No. Nononono. This had never happened before! Sam wasn’t supposed to leave him!_

“Sammy? Sammy, please. Don’t… don’t do this. Don’t give up. You can’t just…” He trailed off when he realised that Sam wasn’t breathing. 

“Cas,” Dean pleaded as he whipped his glassy gaze to his angel’s face. “Cas, please. Fix this. Do something.”

Castiel immediately crouched beside Dean and poured his diminished grace into Sam’s body, squeezing his eyes shut as he focused. After a few moments, he opened them with a haunted expression and he seemed to grow pale as he slowly turned his gaze to Dean. 

He shook his head, shocked. “He… Dean… He’s gone. There’s nothing I can do.” He turned back to Sam, looking rather nauseous. “I can’t…” 

There was a tightness in Dean’s chest stopping him from breathing. _How could Sam be dead?_ He shook his head frantically and rattled his brother’s shoulders. “Sam, wake up. Please, wake up.” He was going to be sick. This couldn’t be how it ended. 

He could barely see through his own tears and he realised that he was crying Sam’s name like a mantra, practically praying for him to return. Arms tugged him into a warm body and he sobbed openly against Castiel’s shoulder, clutching at his angel as his voice grew hoarse with desperation. He felt Castiel’s breaths hitch and he realised that the angel was crying with him, face buried in his hair as he clung to Dean. 

They stayed with Sam for three hours before finally gathering the strength to bring him home for a proper hunter’s funeral.

* * *

He begged Jack to bring Sam back every night after that and each night, Jack would patiently explain that the Winchesters had chosen to write their own stories and as such, they had to accept the consequences of their actions. They could not keep being revived as they once had. Besides, Sam was in heaven and he was happy – wasn’t that what Dean had wanted? 

Dean continued to plead for an exception, just this once.

Jack stopped answering in the third month.

* * *

Castiel asked for Sam’s return at least twice, albeit far more subtly than Dean. Jack frowned disapprovingly and told him that he knew better than to ask for that. Castiel attempted to guilt trip him by stating that he and the Winchesters had saved Jack on multiple occasions _and_ had practically raised him. 

Jack pointed out that Dean had been happy to kill him, _twice_.

Castiel stopped asking for Sam’s resurrection.

* * *

They both had good days and bad days. This was a bad day for both of them. 

Six months after Sam had died, six months after they’d laid his body on a burning pyre, six months after they had quit hunting for good, Dean found himself scowling at a car that should have been simple to fix but was proving too difficult for his scrambled mind to comprehend. 

He could feel Castiel watching him from the corner of the garage, arms crossed impatiently. The angel had picked up a job as a high school teacher (using a bit of waning angel mojo) and it was obvious that he was tired and wanted to go home. Currently, the only thing stopping him from doing that was Dean and his penchant for resolving negative emotions by working on broken cars. 

“Go home and I’ll catch up to you later,” Dean grunted as he fingered through his tool kit, searching.

Castiel squared his jaw and guilt tugged at Dean’s hearts strings. His angel was clearly having a bad day too. 

“I can wait.”

 _He wants to be with you. He needs you. Stop working._

Dean ignored the little voice at the back of his mind and made his way towards the broken _Mondeo._ He had never thought modern cars were built to last – not like his Baby was. 

“Go home, Cas,” Dean sighed as he eased himself under the car. The jack creaked beneath the weight of the vehicle.

 _Honestly. Who fitted a three-litre engine in a Ford Mondeo_ Estate _? It was like welding a spoiler onto the back of a double-decker bus._

“I want to wait,” Castiel replied curtly, voice tinged with annoyance.

“Fine,” grumbled Dean as he eyed the various shafts and shackles and other pieces of car anatomy. Another groan from the jack; it had been doing that all afternoon and Dean had tuned it out after the first four hours. 

“Anything I can help you with?” Cas asked after a few minutes.

Dean closed his eyes and tried not to draw similarities between the cold metal above him and the cold body he had placed on the pyre six months ago. 

“Can you pass me the quarter wrench?” he asked gently, hoping that Cas understood that he wasn’t angry with him.

The tool appeared beneath the car and Dean made sure to ‘accidentally’ brush Cas’ fingers as he accepted the wrench, just to brighten his angel up a little. 

Dean set to work again, smiling weakly when Castiel sat cross-legged beside the car, watching him silently. They did this sometimes and Dean allowed himself to enjoy the moment, because today had been rough without Sam. He was grateful for his angel, even if he didn’t have the energy to say it. 

There was a loud _bang_ and a gasp from Cas as the car plummeted towards Dean’s face.

* * *

“Everybody’s gonna die, Cas, _everybody._ ” Dean stared at the floor as waves of helplessness swept over him, dragging him under, drowning him. The words had taken on a new meaning and he meant them with every fibre of his being. “I can’t stop it.” It was true – he couldn’t stop the time loop. Either Sam or Cas died one way or another, but it didn’t matter anyway, because Dean _always_ died and got dragged back to this moment. 

Castiel turned to the door and a rune ignited upon its surface in fiery orange.

“She’s gonna get through that,” Dean sighed without much enthusiasm. Or care at all, really. What was the point of all this if he couldn’t save Cas _and_ Sam? 

“I know,” Castiel said hopelessly.

Dean watched his eyebrows furrow briefly in thought. He didn’t want the angel to die here but honestly, he didn’t think he had the energy to keep fighting. The result was always the same anyway. Might as well let nature take its course. 

“Wait, there is… there’s one thing she’s afraid of. There’s one thing strong enough to stop her. When Jack was dying, I… I made a deal to save him.” 

Dean closed his eyes. He didn’t want to listen to this again. Not when he knew where it led.

“The… the price was my life,” Castiel said solemnly and Dean stared at him sadly. “When I experienced a moment of true happiness, the Empty would be summoned and it would take me, forever.” 

“I can’t,” Dean whispered and Castiel paused, tilting his head in confusion. “I can’t do this again,” Dean said softly.

Castiel’s brows pinched. “I… I don’t understand.” 

Dean shook his head. “I know you don’t, angel. And it hurts so much that you don’t.”

Castiel looked startled by the pet name and then his eyes widened in alarm. “Dean? What are you talking about?” 

Dean laughed and he wondered if he was going mad. “Doesn’t matter. You won’t remember anyway. You never do.” He looked up, wondering if Chuck was snickering or if he was as clueless as everyone else. 

“I want this to end,” he said seriously, staring Cas dead in the eye. “I just want it to stop.”

Castiel was growing more and more distressed. “What do you mean? You’re not making any sense.” 

Dean glanced at the door and contemplated throwing himself onto Billie’s scythe to make her job easier.

“I know. It’s okay. None of this makes any sense to me either,” Dean murmured as he shuffled towards the door. 

“Dean? What are you doing? Dean!”

He paused as he curled his fingers around the handle and he smiled to himself, refusing to look back at Castiel. 

“The only bit of this that makes any sense is that I love you.” He chuckled quietly. “I have no idea why you love me though. That makes absolutely _no_ sense. I’m a mess. A screw-up. A _murderer_. Can’t even die right, apparently,” he said as he gestured around them vaguely. “Nope. No heaven or hell for me. Just an endless loop. Save my angel, lose my brother. Save my brother, lose my angel. Can’t win.” 

He sighed as he heard the tell-tale sounds of the Empty appearing. “Right on cue,” he mumbled and he threw the door open, allowing Billie to storm inside. 

He turned to Castiel with a tired smile and the angel stared at him pityingly, looking calmer than his earlier shout suggested.

“I know about your deal,” Dean offered, entirely ignoring Billie, to her surprise. “It was a stupid deal.” 

“Yes, it was,” Castiel agreed, voice oddly firm. The Empty gurgled gleefully behind him.

Dean shoved his hands into his pockets. “I really do love you. I’ve said it a hundred times already, but I’m gonna tell you again because you’re about to die and you deserve to know.” 

A smile curved Castiel’s lips. “Thank you, Dean. That makes me… very happy.”

The Empty threw out a black limb and grasped Billie before she could lop Dean’s head off with her scythe. A second tendril slithered towards Castiel. 

“Goodbye, Cas,” Dean said softly as the tendril curled around the angel’s leg.

Castiel frowned and raked his gaze over Dean carefully. “We’ve caused you so much pain,” he said cryptically before raising his hand. 

Suddenly, the Empty halted in its tracks and Billie froze with it, as though someone has pressed the pause button on a cosmic remote. 

Dean looked around wildly, eyes wide as Castiel approached him.

“Who are you?” Dean asked immediately, taking a step backwards and narrowing his eyes at the creature wearing Cas’ face. “What have you done with Cas?” 

The creature seemed to slump before shaking its head slowly. “Dean… I… I’m so sorry. This was never meant to happen. We just… We needed more time. To reboot heaven. You passed quicker than we expected and we… we had to think of something.” The creature scowled and glanced between Billie and the Empty. “If we’d have known this would happen… If _I’d_ known this is where you’d be sent…” Sorrowful blue eyes met green. “I’m so sorry. I should have worked it out quicker.” 

Dean slowly relaxed as he eyed Castiel’s face warily. “…Cas?”

A nod. “Yes, Dean. I'm the real Castiel. The others were part of the program. Projections, if you will.” 

Dean’s head hurt and he rubbed at his eyes to relieve the pain. “I… I don’t understand. What program? Where am I? Why do I keep getting thrown back in time? And why can you suddenly _control_ it?” He gestured to the frozen scenery around them. 

Castiel sighed and waved his hand, and the bunker melted away, taking Billie and the Empty with it. Instead, Dean found himself standing on an abandoned road in the middle of a collection of fields. The place was eerily quiet – not a bird singing in the few trees dotted around and there was no air movement, nor scents of any kind. There was also a space to Dean’s right that he couldn’t quite look at, or maybe he could and his brain just could understand what it was seeing so was choosing to block it out, leaving it as a patch of nothingness that he couldn’t directly stare into. 

“Where… where are we?”

“Heaven,” sighed Castiel as he frowned at the space Dean couldn’t look at. He waved his hand and the space became part of the greenery. “There are lots of… glitches.” 

Dean’s eyes widened and he glanced around again. “Wait, heaven? So, I’m…?”

“Dead?” Castiel finished with an apologetic glance. “Yes. As I said, you died quicker than we anticipated – on a rebar, of all things – and heaven was severely damaged. Too few angels left to keep it running so it just… fell into a state of disrepair. The personal heavens for each human had all shut down and everyone was congregating in corridors when Jack and I arrived. Heaven was almost on the verge of spitting humans out to keep itself from imploding. There was no way we could have brought you back here.” 

Castiel shook his head. “Every human here had to be sent into a time loop because there was nowhere else to put them whilst we fixed heaven. Jack devised a program that would send them to their happiest moments and allow them to relive them over and over.” Castiel clenched his fists angrily. “Except the program was thrown together hastily by the two of us and apparently, it has a few glitches. If we had known that your program had a fault, I would have intervened a lot sooner." He gazed at Dean sorrowfully. 

“Wait, a fault? What do you mean?” Dean asked, brain aching.

“We chose your 'moment' for you because your life is complicated,” Castiel sighed. “We didn’t want you to ask too many questions so we made one up for you. Remember Mrs. Butters? We created her for you. It isn’t how the program was designed to run though, so we had to set some limitations. You had to remain in the bunker with her and we couldn’t have too many ‘characters’ as the program couldn’t handle so many variables – that’s why I wasn’t there. Having Jack there was a risk, but we reduced his powers and it made things a little easier. You seemed to enjoy Mrs. Butters’ company, anyway.” 

Dean shook his head. “But she… she tried to kill Jack!”

“As I said, the program glitched,” scowled Castiel. “And we weren’t aware of it. The program began picking out your memories and recreating them, as it was initially created to do. Then, it searched for your happiest moment, which apparently…” Castiel dropped his gaze uncomfortably and lowered his voice. “Which, apparently… was the moment I confessed my feelings for you.” 

“And it… created a loop for me,” Dean realised. “Because it didn’t understand that my happiest moment led to the worst moment of my life.” 

Castiel refused to meet his gaze as he nodded, ashamed. “It took us far too long to figure out that something was amiss because we were so busy with heaven and the angels that Jack rescued from the Empty.” 

Dean frowned. “Wait, you said I was in a loop with Mrs. Butters, but I only remember that one time with her. It was a long time, sure, but nothing repeated.” 

“Your memory was erased after each loop in order for the program to complete with as few variables as possible. Everyone’s was. If you start messing with the loop and changing your reactions to certain situations, the program has to calculate a new situation in response and… things were strained as it was. It was easier to keep reliving the exact same loop until heaven was fixed,” Cas murmured. 

“But… why could I remember each time I was thrown back to… um… _that_ point? Why didn’t it wipe my memory?”

Castiel sighed and shrugged. “I suppose it was part of the glitch. It’s also why you kept dying over and over again. The program wasn’t designed to run scenarios for over eight months. Once you got to the end of that designated time, the program just… stopped working. Hence the car that fell on you. And the reason why ‘characters’ stopped interacting with you. Sam’s death, my deaths, Jack’s disappearance… Even Michael. He vanished from the program altogether, although I’m not entirely certain you noticed. The program couldn’t cope with all those people living their own lives inside your loop, so it found ways to get rid of them.” 

Dean wanted to sit down. Preferably with a stiff drink.

“So… let me get this straight. Those ‘resets’ were part of a program that you and Jack created because I died and heaven was out of service. Except the program glitched and I was catapulted out of my happy little nymph illusion and thrown into an _actual_ memory that the program then couldn’t sustain, which led to me struggling with crippling grief and emotional trauma as I watched my friends and family die over and over, and you’ve only just found out about all of this _now?_ Is that about right?” 

Castiel nodded embarrassedly. “That sums it up rather nicely. Yes.”

Dean closed his eyes and exhaled heavily. “Great. One last question?” 

“Go on?”

Dean stared hard at the angel. “Are you alive? Or is this still part of the illusion? Because, you definitely died, right? I remember that. So, are you actually here or is this part of the program?” 

Castiel stared back miserably. “Yes, Dean. I’m alive. Jack made a deal with the Empty. He promised to remove all the angels and demons so that it could sleep for the rest of eternity.” He sagged. “That’s… that’s another thing we have to work out now. Where angels and demons go when they die.” 

Dean closed his eyes, sucked in a deep breath, and when he reopened them, he paced towards his angel and tugged him in for a bone-crushing hug. 

“If you died the way I remember you dying that first time, then that means I never told you how I feel.”

“Well, actually, I’ve seen your life in the program and on multiple occasions, you admitted-” 

“Shut up, Cas and let me tell you that I love you.”

“…Okay, Dean.” 

Dean nestled into Cas’ warmth and kissed his neck tenderly. “I love you. And you’re an idiot, because I’ve suffered through emotional _hell_ because of you. But I love you and I need you and you’re the best friend I’ve ever had and I didn’t tell you that enough whilst we were both alive.” 

Cas’ arms snaked around him. “I’m sorry I put you through all that. It wasn’t my intention to make you suffer.”

“You can pay for my therapy,” Dean teased before he cupped his angel’s cheek and kissed him soundly on the lips. He pulled away and grinned at the dazed expression on Cas’ face. 

“I never get tired of that,” Dean grinned and Castiel sputtered for a moment before shaking his head quickly.

“I can assure you that we’ve _never_ done that before.” 

Dean grinned and looked around at the lacklustre heaven. “Hey, fancy a hand with this heaven stuff? Maybe a human’s perspective would help, since it’s… y’know, designed for humans.” 

Cas tilted his head. “It was supposed to be a surprise for when you returned from your loop, but I suppose you don’t wish to return to the program, even if we alter it?” 

Dean shuddered. “Hard pass.” He perked up. “Besides, I wanna see Jack!”

Castiel quirked a smile. “He will be thrilled to have you with us. As am I.” 

Castiel gently grasped his arm and suddenly, two huge, impossible wings unfurled from his back, midnight blue and striped with black in a way that reminded Dean of a magpie. He gaped at them and wondered why his eyes didn’t burn. Castiel chuckled. 

“You’re in heaven,” he reminded. “Your perception of the different planes of existence has shifted. There’ll be a lot of things you can see and hear and taste that you couldn’t before. You can ask Bobby all about it.” 

Dean perked up. “Bobby’s here?”

Castiel rolled his eyes. “He kept breaking the program. We created a house for him instead – the only human currently in heaven.” 

Dean laughed and Castiel smiled at the sound before straightening his wings, ready to take off.

“Wait, how’s Sam?” Dean asked quickly, worriedly. “Is he… is he doing okay without me?” 

Castiel frowned sadly. “Ah… not… not really. But he’ll manage. Eventually.”

Dean slumped in disappointment and Castiel glanced off into the distance thoughtfully. 

“Perhaps we can give him a little nudge in the right direction?” Cas suggested airily.

Dean grinned and Castiel held him tight as he took flight.

**Notes for the Chapter:**

> Warning: Dean gets very down and depressed in the middle of this so beware 
> 
> Got a little carried away with this one... Hope you enjoyed!

**Author's Note:**

> After being mildly disappointed and confused after 15x19, my friend and housemate set me a challenge to write 50 shorts to 50 words she came up with. Each must be unrelated and should be written as a potential ending to the show. They can tie up loose ends, fill in plot holes, or go in completely unexpected directions, but they must be endings. The challenging part is trying to fit them into canon and make them at least semi-believable. Hope you enjoy this mess, 'Flucky'.
> 
> Also, to anyone who wants to take on this challenge with me, the chapter titles are the prompts!


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